JPH0764771B2 - Method for producing polyfluoroacetal - Google Patents
Method for producing polyfluoroacetalInfo
- Publication number
- JPH0764771B2 JPH0764771B2 JP62177218A JP17721887A JPH0764771B2 JP H0764771 B2 JPH0764771 B2 JP H0764771B2 JP 62177218 A JP62177218 A JP 62177218A JP 17721887 A JP17721887 A JP 17721887A JP H0764771 B2 JPH0764771 B2 JP H0764771B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- producing
- palladium
- trifluoropropane
- polyfluoroacetal
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000002940 palladium Chemical class 0.000 claims description 5
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- VMGIQGADPKWJFA-UHFFFAOYSA-N 1,1,1-trifluoro-3,3-dimethoxypropane Chemical compound COC(OC)CC(F)(F)F VMGIQGADPKWJFA-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- 229920004482 WACKER® Polymers 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- -1 alkenyl ether Chemical compound 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001879 copper Chemical class 0.000 description 2
- 229960003280 cupric chloride Drugs 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical class O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- UTMIEQASUFFADK-UHFFFAOYSA-N 3,3,3-trifluoropropanal Chemical compound FC(F)(F)CC=O UTMIEQASUFFADK-UHFFFAOYSA-N 0.000 description 1
- CMJLMPKFQPJDKP-UHFFFAOYSA-N 3-methylthiolane 1,1-dioxide Chemical compound CC1CCS(=O)(=O)C1 CMJLMPKFQPJDKP-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229960002089 ferrous chloride Drugs 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 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
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000009751 slip forming Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- 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〕 本発明は医農薬中間体、潤滑剤、表面処理剤等として有
用なポリフルオロアルキルカルボン酸の原料となる1,1
−ジアルコキシ−3,3,3−トリフルオロプロパン等のポ
リフルオロアセタールの製造法に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial field of application] The present invention is a raw material for polyfluoroalkylcarboxylic acids useful as intermediates for medical and agricultural chemicals, lubricants, surface treatment agents, etc.
The present invention relates to a method for producing a polyfluoroacetal such as dialkoxy-3,3,3-trifluoropropane.
〔従来の技術〕 1,1−ジアルコキシ−3,3,3−トリフルオロプロパンの製
造法としては対応するアルケニルエーテルに塩基の存在
下アルコールを作用させることにより得る方法がある
（USP2883429）がこのアルケニルエーテルはトリフルオ
ロプロペンから多段階の反応を経て合成されるもので、
極めて高価でありまた入手困難な化合物である。[Prior Art] As a method for producing 1,1-dialkoxy-3,3,3-trifluoropropane, there is a method of reacting a corresponding alkenyl ether with an alcohol in the presence of a base (USP2883429). Alkenyl ether is synthesized from trifluoropropene through multi-step reaction,
It is a compound that is extremely expensive and difficult to obtain.
本発明者は、工業的に入手できる安価な原料であるポリ
フルオロアルケンから容易にポリフルオロアセタールを
得ることができることを見出し本発明に到ったものであ
る。The present inventors have found that polyfluoroacetal can be easily obtained from polyfluoroalkene, which is an industrially available inexpensive raw material, and have completed the present invention.
すなわち本発明はパラジウム塩の存在下、3,3,3−トリ
フルオロプロペンと炭素数１または２のアルコールとを
酸素雰囲気で反応させることを特徴とする1,1−ジアル
コキシ−3,3,3−トリフルオロプロパンの製造法であ
る。That is, the present invention is characterized by reacting 3,3,3-trifluoropropene and an alcohol having 1 or 2 carbon atoms in an oxygen atmosphere in the presence of a palladium salt. 1,1-dialkoxy-3,3, This is a method for producing 3-trifluoropropane.
3,3,3−トリフルオロプロペンをパラジウム塩（例えば
塩化パラジウム）を含むアルコール中で反応させると次
の反応が進行する。When 3,3,3-trifluoropropene is reacted in an alcohol containing a palladium salt (for example, palladium chloride), the next reaction proceeds.
これはワッカータイプの反応に属すると考えられるが、
一般的ワッカー反応では２位の炭素が酸化されるが、本
発明の方法においては、１位のみが極めて選択的に酸化
されるものである。 This is thought to belong to the Wacker type reaction,
In the general Wacker reaction, carbon at the 2-position is oxidized, but in the method of the present invention, only the 1-position is extremely selectively oxidized.
この反応は化学量論的な反応であるので、パラジウム塩
を触媒的に働かせようとする場合は、反応により生成し
たPd金属をPd2価に酸化させるための酸化剤及び還元さ
れた酸化剤を酸化するための酸素（０）存在下でこの反
応を行なえばよい。Since this reaction is a stoichiometric reaction, when the palladium salt is intended to act catalytically, the Pd metal produced by the reaction is oxidized by the oxidant and the reduced oxidant. This reaction may be carried out in the presence of oxygen (0).
本発明で用いるアルコールとしては、炭素数１〜12のア
ルコール、エチレングリコール、プロパンジオール等の
ジオールが挙げられる。Examples of the alcohol used in the present invention include alcohols having 1 to 12 carbon atoms, diols such as ethylene glycol and propanediol.
パラジウム系触媒としては、塩化パラジウム、酢酸パラ
ジウム、硫酸パラジウム、硝酸パラジウム等のパラジウ
ム塩あるいは金属パラジウムも使用できる。ただし、金
属パラジウムの場合には、反応系においてPd2価になる
ようにしておく必要がある。As the palladium-based catalyst, palladium salts such as palladium chloride, palladium acetate, palladium sulfate, and palladium nitrate, or metallic palladium can also be used. However, in the case of metallic palladium, it is necessary to make Pd2 valence in the reaction system.
酸化剤としては、塩化第１銅、塩化第２銅、酢酸銅等の
銅塩、塩化第１鉄、塩化第２鉄等の鉄塩、ヘテロポリリ
ン酸、Ｐ−ベンゾキノン等が可能である連続化を考えた
場合、銅塩が最も適している。As the oxidizing agent, copper salts such as cuprous chloride, cupric chloride, and copper acetate, iron salts such as ferrous chloride and ferric chloride, heteropolyphosphoric acid, P-benzoquinone, and the like can be continuously formed. When considering, copper salt is most suitable.
また、溶媒は特に必要としないが、用いることにより反
応速度を増し副生成物の生成を抑制することができる。
有機溶媒としては、酢酸、1,4−ジオキサン、N,N−ジメ
チルホルムアミド、Ｎ−メチルホルムアミド、ジメチル
スルホキシド、３−メチルスルホランのようなスルホラ
ン類が可能であり、このうち酢酸、1,4−ジオキサン、
スルホラン類が特に適している。In addition, a solvent is not particularly required, but by using it, the reaction rate can be increased and the production of by-products can be suppressed.
As the organic solvent, sulfolanes such as acetic acid, 1,4-dioxane, N, N-dimethylformamide, N-methylformamide, dimethylsulfoxide, and 3-methylsulfolane can be used. Among them, acetic acid, 1,4- Dioxane,
Sulfolanes are particularly suitable.
また、この反応は、微量のＦイオンを生成するため、触
媒の活性低下を防ぐために、また、反応器材を保護する
ためにも、水酸化アルミニウム等のＦ除去剤を添加する
ことが好ましい。In addition, since this reaction produces a small amount of F ions, it is preferable to add an F remover such as aluminum hydroxide in order to prevent a decrease in the activity of the catalyst and also to protect the reactor material.
また、反応温度はとくに限定されないが、室温から150
℃の範囲が実際的であり、より好ましくは、反応速度の
面からは高い方が好ましく、また90℃以上では副反応が
起り易く、選択率が低下するため50〜90℃程度が好まし
い。また、反応は常圧でも加圧系でも行なうことがで
き、反応速度を高める意味からは、加圧系が望ましい。The reaction temperature is not particularly limited, but may be from room temperature to 150
The range of ℃ is practical, more preferably higher from the viewpoint of reaction rate, and at 90 ° C or higher, side reactions are likely to occur and the selectivity is lowered, so that it is preferably about 50 to 90 ° C. The reaction can be carried out under normal pressure or under pressure, and a pressure system is preferable from the viewpoint of increasing the reaction rate.
本発明で得られるポリフルオロアセタールは加水分解に
より容易にアルデヒドすることができ、反応で生じる水
をこの目的に利用することもできる。すなわち用いるア
ルコール量より過剰のポリフルオロアルケンを導入する
ことにより、アルデヒドとアセタールの混合物を得るこ
とができる。アルデヒドはポリフルオロアセタールに比
較して安定性に劣るため、アセタールとして貯蔵し、必
要時に加水分解をおこないアルデヒドを得るようにする
ことも好ましい。The polyfluoroacetal obtained in the present invention can be easily converted into an aldehyde by hydrolysis, and the water produced by the reaction can be used for this purpose. That is, a mixture of aldehyde and acetal can be obtained by introducing polyfluoroalkene in excess of the amount of alcohol used. Since aldehydes are less stable than polyfluoroacetals, it is also preferable to store them as acetals and hydrolyze them when necessary to obtain aldehydes.
以下、本発明を実施例及び第１表により、さらに詳細を
説明する。Hereinafter, the present invention will be described in more detail with reference to Examples and Table 1.
実施例１ メタノール250g、塩化パラジウム2.0g、塩化第２銅3.85
g、水酸化アルミニウム3.0gを仕込んだガラス製オート
クレーブを60℃に保ち、これに撹拌下、トリフルオロプ
ロペンと酸素をモル比2:1になるように調整しながら、
全圧を8kg/cm2に設定して連続的に導入していった。こ
れを６時間続けた後、中味を取り出し、蒸留操作を行な
ったところ、1,1−ジメトキシ−3,3,3−トリフルオロプ
ロパンの生成量は95.4gであり、選択率は93.7％であ
り、残部はトリフルオロプロパナールであった。Example 1 250 g of methanol, 2.0 g of palladium chloride, cupric chloride 3.85
g, keeping a glass autoclave charged with 3.0 g of aluminum hydroxide at 60 ° C., while stirring and adjusting trifluoropropene and oxygen so that the molar ratio becomes 2: 1,
The total pressure was set to 8 kg / cm 2 and continuous introduction was performed. After continuing this for 6 hours, the contents were taken out and subjected to a distillation operation. The amount of 1,1-dimethoxy-3,3,3-trifluoropropane produced was 95.4 g, and the selectivity was 93.7%. The balance was trifluoropropanal.
1,1−ジメトキシ−3,3,3−トリフルオロプロパンの分析
データは次のとおりである。The analytical data of 1,1-dimethoxy-3,3,3-trifluoropropane are as follows.
沸点 97.2℃/760mmHg1 H−NMR（アセトンd6）： δ2.43（q,d,JF-H＝10.5Hz,JH-H＝6Hz,CH2）、 3.33（S,CH3O）、 4.66（t,CH）19 F−NMR（アセトン−d6）： 実施例２〜９ 実施例１と同様にして各条件を第１表に示すとおり変化
させ、製造を行なった。この結果を第１表に示す。Boiling point 97.2 ° C / 760 mmHg 1 H-NMR (acetone d 6 ): δ2.43 (q, d, J FH = 10.5 Hz, J HH = 6 Hz, CH 2 ), 3.33 (S, CH 3 O), 4.66 (t , CH) 19 F-NMR (acetone-d 6 ): Examples 2 to 9 In the same manner as in Example 1, each condition was changed as shown in Table 1, and the production was performed. The results are shown in Table 1.
〔発明の効果〕 本発明は工業的に入手可能で安価な原料であるトリフル
オロプロペンを用いて容易に且つ収率よく1,1−ジアル
コキシ−3,3,3−トリフルオロプロパンを得ることがで
きるものである。また、この1,1−ジアルコキシ−3,3,3
−トリフルオロプロパンは加水分解により容易にアルデ
ヒドを与えるため、対応するアルデヒドの製造にも適し
た方法である。 [Advantages of the Invention] The present invention is capable of obtaining 1,1-dialkoxy-3,3,3-trifluoropropane easily and in good yield by using trifluoropropene, which is an industrially available and inexpensive raw material. Is something that can be done. In addition, this 1,1-dialkoxy-3,3,3
-Trifluoropropane is a suitable method for the production of the corresponding aldehydes, since it easily gives aldehydes by hydrolysis.
───────────────────────────────────────────────────── 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 Ｃ０７Ｃ 41/54 // Ｃ０７Ｂ 61/00 ３００ ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 6 Identification code Internal reference number FI technical display location C07C 41/54 // C07B 61/00 300
Claims (2)
オロプロペンと炭素数１または２のアルコールとを酵素
雰囲気中で反応させることを特徴とする1,1−ジアルコ
キシ−3,3,3−トリフルオロプロパンの製造法。1. A 1,1-dialkoxy-3, which comprises reacting 3,3,3-trifluoropropene with an alcohol having 1 or 2 carbon atoms in an enzyme atmosphere in the presence of a palladium salt. A method for producing 3,3-trifluoropropane.
とを特徴とする請求項１記載の1,1−ジアルコキシ−3,
3,3−トリフルオロプロパンの製造法。2. A 1,1-dialkoxy-3, as claimed in claim 1, characterized in that aluminum hydroxide is additionally present.
A method for producing 3,3-trifluoropropane.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62177218A JPH0764771B2 (en) | 1987-07-17 | 1987-07-17 | Method for producing polyfluoroacetal |
| GB8720398A GB2196002B (en) | 1986-09-05 | 1987-08-28 | Preparation of polyfluoroaldehydes and polyfluoroacetals |
| US07/092,680 US4837366A (en) | 1986-09-05 | 1987-09-03 | Preparation of polyfluoroaldehydes and polyfluoroacetals |
| IT21809/87A IT1222601B (en) | 1986-09-05 | 1987-09-04 | Prepn. of poly:fluoro-aldehyde(s) and poly:fluoro-acetal(s) |
| FR878712318A FR2603580B1 (en) | 1986-09-05 | 1987-09-04 | PROCESS FOR THE PREPARATION OF AN ORGANIC POLYFLUORIDE COMPOUND |
| DE19873729734 DE3729734A1 (en) | 1986-09-05 | 1987-09-04 | METHOD FOR PRODUCING POLYFLUORALDEHYDES AND POLYFLUORACETALS |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62177218A JPH0764771B2 (en) | 1987-07-17 | 1987-07-17 | Method for producing polyfluoroacetal |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6422836A JPS6422836A (en) | 1989-01-25 |
| JPH0764771B2 true JPH0764771B2 (en) | 1995-07-12 |
Family
ID=16027225
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62177218A Expired - Lifetime JPH0764771B2 (en) | 1986-09-05 | 1987-07-17 | Method for producing polyfluoroacetal |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0764771B2 (en) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS559029A (en) * | 1978-07-06 | 1980-01-22 | Sagami Chem Res Center | Preparation of 1,1-dialkoxy-2-phenylethane |
| JPS5626829A (en) * | 1979-08-11 | 1981-03-16 | Toyotama Koryo Kk | Preparation of phenylacetaldehyde dialkyl acetal |
-
1987
- 1987-07-17 JP JP62177218A patent/JPH0764771B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6422836A (en) | 1989-01-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4356333A (en) | Process for preparing n-octadienol | |
| EP0425643B1 (en) | Octadienyl ethers and a process for making octadienyl ethers | |
| US5077447A (en) | Process for making olefins | |
| JP2523753B2 (en) | Method for producing 2,3-dichloropyridine | |
| US6020517A (en) | Process for production of benzonitrile and benzyl alcohol | |
| US4837366A (en) | Preparation of polyfluoroaldehydes and polyfluoroacetals | |
| JPH0237212B2 (en) | ||
| EP0070665B1 (en) | Process for oxidising phenol to p-benzoquinone | |
| JPH085838B2 (en) | Method for producing biphenyltetracarboxylic acid | |
| JPH0764771B2 (en) | Method for producing polyfluoroacetal | |
| US4379939A (en) | Preparation of nitrogen fertilizers from oxalate esters prepared by the oxidative carbonylation of alcohols over noble metal catalysts utilizing regenerable 2,5-cyclohexadiene-1,4-dione oxidants | |
| JP3026114B2 (en) | Production method of organic carbonate | |
| EP0259788B1 (en) | Process for producing carbonic acid ester | |
| US4000185A (en) | Process for the production of 1,4-diacyloxy-2-butene from butadiene | |
| JPS5843936A (en) | Manufacture of glycol aldehyde | |
| JPS6363633A (en) | Production of 3,3,3-trifluoropropanal | |
| EP0317975B1 (en) | Process for the production of saturated neo-alcohols | |
| JP2548590B2 (en) | Method for selective oxidative carbonylation of conjugated dienes | |
| JP3237541B2 (en) | Reduction method of aldehyde or ketone | |
| JP3489179B2 (en) | Method for producing hydrofluorocarbon | |
| US4482735A (en) | Process for preparation of methyl methoxyacetate | |
| EP0144252B1 (en) | Process for the oxyacylation of butenes to linear acetates | |
| US4450293A (en) | Preparation of α-hydroxyisobutyric acid using a thallic halide catalyst | |
| JP2918713B2 (en) | Method for producing carbonate ester | |
| US4602103A (en) | Process for the oxidation of butenes to linear acetates |