JPS6330399B2 - - Google Patents
Info
- Publication number
- JPS6330399B2 JPS6330399B2 JP60272688A JP27268885A JPS6330399B2 JP S6330399 B2 JPS6330399 B2 JP S6330399B2 JP 60272688 A JP60272688 A JP 60272688A JP 27268885 A JP27268885 A JP 27268885A JP S6330399 B2 JPS6330399 B2 JP S6330399B2
- Authority
- JP
- Japan
- Prior art keywords
- electrolytic
- electrolytic fluorination
- reaction
- weight
- added
- 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
- 238000003682 fluorination reaction Methods 0.000 claims description 20
- -1 aliphatic tertiary amine Chemical class 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 7
- 150000003464 sulfur compounds Chemical class 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000000654 additive Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- RVZRBWKZFJCCIB-UHFFFAOYSA-N perfluorotributylamine Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)N(C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F RVZRBWKZFJCCIB-UHFFFAOYSA-N 0.000 description 5
- 239000012261 resinous substance Substances 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 125000005360 alkyl sulfoxide group Chemical group 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 3
- MMCXKYPKYQMCRM-UHFFFAOYSA-N 2-methyl-3,4,4a,5,6,7,8,8a-octahydro-1h-isoquinoline Chemical compound C1CCCC2CN(C)CCC21 MMCXKYPKYQMCRM-UHFFFAOYSA-N 0.000 description 2
- CMJLMPKFQPJDKP-UHFFFAOYSA-N 3-methylthiolane 1,1-dioxide Chemical compound CC1CCS(=O)(=O)C1 CMJLMPKFQPJDKP-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005868 electrolysis reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000005796 dehydrofluorination reaction Methods 0.000 description 1
- 238000004334 fluoridation Methods 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- MRQNKLRMROXHTI-UHFFFAOYSA-N perfluoro-N-methyldecahydroisoquinoline Chemical compound FC1(F)C(F)(F)C(F)(F)C(F)(F)C2(F)C(F)(F)N(C(F)(F)F)C(F)(F)C(F)(F)C21F MRQNKLRMROXHTI-UHFFFAOYSA-N 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
Landscapes
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、電解フツ素化方法に関する。[Detailed description of the invention] [Industrial application field] The present invention relates to an electrolytic fluorination method.
有機物を電解フツ素化すると、副生する樹脂状
物質が陽極表面を覆い、電流が流れにくくなり、
有意量のフツ素化物を製造することができなくな
ることがよくある。
When organic matter is electrolytically fluorinated, a by-product resinous substance covers the anode surface, making it difficult for current to flow.
It is often impossible to produce significant amounts of fluoride.
樹脂状物質が電極表面に付着するのを防止する
目的で、不飽和または飽和環状スルホン等の添加
剤を電解フツ素化時添加しておくことが提案され
たことがある（特公昭53−27246号公報および特
開昭57−70283号公報参照）。しかし、目的フツ素
化物が常温で液体の場合、前記環状スルホンの電
解フツ素化物も常温で液体であるので（環状スル
ホンも電解フツ素化される）、電解フツ素化反応
混合物は、目的フツ素化物の他、前記環状スルホ
ンの電解フツ素化物を含んでおり、電解フツ素化
反応後、目的フツ素化物と前記環状スルホンの電
解フツ素化物を分離しなければならない。目的フ
ツ素化物の中には、前記環状スルホンの電解フツ
素化物と蒸留等では分離し難いものがあり、容易
に目的フツ素化物と分離することができる添加剤
が望まれていた。 It has been proposed to add additives such as unsaturated or saturated cyclic sulfones during electrolytic fluorination in order to prevent resinous substances from adhering to the electrode surface (Japanese Patent Publication No. 53-27246). (See Japanese Patent Application Laid-open No. 57-70283). However, if the target fluorinated product is liquid at room temperature, the electrolytic fluorinated product of the cyclic sulfone is also liquid at room temperature (cyclic sulfone is also electrofluorinated), so the electrolytic fluorination reaction mixture has the target fluorinated product. In addition to the fluorinated product, it contains an electrolytic fluorinated product of the cyclic sulfone, and after the electrolytic fluorination reaction, the target fluorinated product and the electrolytic fluorinated product of the cyclic sulfone must be separated. Some of the target fluorinated products are difficult to separate from the electrolytic fluorinated product of the cyclic sulfone by distillation, etc., and there has been a desire for an additive that can be easily separated from the target fluorinated product.
本発明者らは、電解フツ素化反応の添加剤につ
いて鋭意検討した結果、ジメチルスルホキシド等
の低級アルキルスルホキシドが、電極表面に樹脂
状物質が付着するのを防止する能力に優れ、また
低級アルキルスルホキシド自身は、電解フツ素化
されると同時に分解して低沸点のパーフルオロ低
級アルキル、SF6、SOF4、SO2F2等になるので、
容易に反応混合物から除くことができることを見
出し、本発明に達したものである。
As a result of intensive studies on additives for electrolytic fluorination reactions, the present inventors found that lower alkyl sulfoxides such as dimethyl sulfoxide have an excellent ability to prevent resinous substances from adhering to the electrode surface. When it is electrolytically fluorinated, it decomposes into low-boiling point perfluoro-lower alkyl, SF 6 , SOF 4 , SO 2 F 2 , etc.
The inventors have discovered that it can be easily removed from the reaction mixture, leading to the present invention.
本発明の目的は、電極表面に樹脂状物質が付着
するのを防止することができ、しかも液状の生成
物と分離することが容易な添加剤を使用する電解
フツ素化方法を提供することである。 An object of the present invention is to provide an electrolytic fluorination method that uses additives that can prevent resinous substances from adhering to the electrode surface and that can be easily separated from liquid products. be.
本発明の要旨は、有機化合物の電解フツ素化に
あたり、式：
Ｒ−SO−R′
（式中、ＲおよびR′は同一または相異なつて炭
素数１〜３の脂肪族基を示す。）
で表わされる硫黄化合物を添加することを特徴と
する電解フツ素化方法に存する。
The gist of the present invention is to perform electrolytic fluorination of organic compounds using the formula: R-SO-R' (wherein R and R' are the same or different and represent an aliphatic group having 1 to 3 carbon atoms.) The present invention relates to an electrolytic fluorination method characterized by adding a sulfur compound represented by:
前記硫黄化合物は、前記有機化合物100重量部
に対し通常0.5〜30重量部、好ましくは１〜５重
量部添加する。硫黄化合物は、最初から全量添加
しておいてよいし、反応中何回かに分けて添加し
てもよい。この硫黄化合物は、特に炭素数が６〜
18の脂肪族第三アミンに適用すると、陽極での樹
脂付着防止効果が顕著である。 The sulfur compound is usually added in an amount of 0.5 to 30 parts by weight, preferably 1 to 5 parts by weight, per 100 parts by weight of the organic compound. The sulfur compound may be added in its entirety from the beginning, or may be added in several portions during the reaction. This sulfur compound especially has 6 to 6 carbon atoms.
When applied to No. 18 aliphatic tertiary amine, the effect of preventing resin adhesion at the anode is remarkable.
前記有機化合物は、電解浴100重量部に対し通
常５〜30重量部、好ましくは10〜20重量部添加す
る。 The organic compound is usually added in an amount of 5 to 30 parts by weight, preferably 10 to 20 parts by weight, per 100 parts by weight of the electrolytic bath.
本発明において、電極の材質および電圧、電流
密度、温度等の反応条件は、一般に採用されてい
るものと同じものでよい。電極の材質は、例えば
ニツケルまたはニツケル合金で、電極間距離は、
通常３〜10mmである。通常、電圧は４〜8V、電
流密度は0.1〜5A／ｄm2、温度は０〜20℃であ
る。 In the present invention, the material of the electrode and reaction conditions such as voltage, current density, temperature, etc. may be the same as those generally employed. The material of the electrodes is, for example, nickel or nickel alloy, and the distance between the electrodes is
Usually 3 to 10 mm. Typically, the voltage is 4-8V, the current density is 0.1-5A/ dm2 , and the temperature is 0-20C.
実施例 １
冷却用ジヤケツトおよびコンデンサーを備えた
電解フツ素化槽に、ニツケル製の陽極３枚と陰極
４枚を間隔６mmで組み込み、１の無水フツ化水
素酸を仕込んだ。
Example 1 In an electrolytic fluoridation tank equipped with a cooling jacket and a condenser, three nickel anodes and four cathodes were installed at a spacing of 6 mm, and 1 of anhydrous hydrofluoric acid was charged.
冷却用ジヤケツトには、−10℃の冷媒を流し、
反応中の電解浴の温度を７〜８℃に保つた。コン
デンサーは、−50℃に冷却した。 -10℃ refrigerant is poured into the cooling jacket.
The temperature of the electrolytic bath during the reaction was maintained at 7-8°C. The condenser was cooled to -50°C.
電解槽内にトリブチルアミン200ｇとジメチル
スルホキシド6.0ｇを仕込み、電流密度2.6A／ｄ
m2（電流10A）で電解フツ素化反応を行つた。 200g of tributylamine and 6.0g of dimethyl sulfoxide are placed in the electrolytic cell, and the current density is 2.6A/d.
Electrolytic fluorination reaction was carried out at m 2 (current 10 A).
240A・Hrごとにトリブチルアミン25ｇとジメ
チルスルホキシド6.0ｇを添加した。反応中、無
水フツ化水素酸は１になるよう、消費された分
を追加した。 25 g of tributylamine and 6.0 g of dimethyl sulfoxide were added for every 240 A·Hr. During the reaction, the amount of hydrofluoric anhydride consumed was added so that the amount was 1.
前記電流密度で3240時間電解フツ素化反応を行
つた。電解電圧は、反応中5.5±0.3Vのほぼ一定
の値を示した。 Electrolytic fluorination reaction was carried out for 3240 hours at the above current density. The electrolysis voltage showed a nearly constant value of 5.5±0.3V during the reaction.
反応混合物は、適宜電解槽底より抜き出した。
6822ｇの反応混合物が得られた。目的物のパーフ
ルオロトリブチルアミンは、その内75.5重量％
（収率40％）あつた。 The reaction mixture was appropriately extracted from the bottom of the electrolytic cell.
6822 g of reaction mixture was obtained. The target product, perfluorotributylamine, is 75.5% by weight.
(Yield 40%) Atsuta.
反応混合物に40重量％のカセイソーダ水溶液と
ジイソブチルアミンの等容量の混合物を加え、５
日間リフラツクスし、脱フツ化水素した。 A mixture of equal volumes of 40% by weight aqueous caustic soda and diisobutylamine was added to the reaction mixture, and 5%
It was refluxed for a day and dehydrofluorinated.
分液後蒸留によりパーフルオロトリブチルアミ
ンを容易に単離することができた。 Perfluorotributylamine could be easily isolated by distillation after separation.
比較例 １
ジメチルスルホキシドを使用しない他は実施例
と同じ手順で電解フツ素化反応を行つた。1000時
間経過したあたりから電圧が少しづつ上昇し、
1500時間後8Vになつた。その時点で電解フツ素
化反応を停止した。Comparative Example 1 Electrolytic fluorination reaction was carried out in the same manner as in Example except that dimethyl sulfoxide was not used. After 1000 hours, the voltage gradually increases,
After 1500 hours it became 8V. At that point, the electrolytic fluorination reaction was stopped.
反応混合物は、適宜電解槽底より抜き出した。
合計1133ｇの反応混合物が得られた。目的物のパ
ーフルオロトリブチルアミンは、その内75.0重量
％（収率15％）あつた。 The reaction mixture was appropriately extracted from the bottom of the electrolytic cell.
A total of 1133 g of reaction mixture was obtained. The target product, perfluorotributylamine, was 75.0% by weight (yield: 15%).
比較例 ２
ジメチルスルホキシドに代えて３−メチルスル
ホランを使用した他は実施例と同じ手順で電解フ
ツ素化反応を行つた。電解電圧は、反応中5.7±
0.3Vのほぼ一定の値を示した。3200時間電解フ
ツ素化反応を行つた。反応混合物は、適宜電解槽
底より抜き出した。6130ｇの反応混合物が得られ
た。目的物のパーフルオロトリブチルアミンは、
その内73重量％（収率35％）あつた。Comparative Example 2 An electrolytic fluorination reaction was carried out in the same manner as in Example except that 3-methylsulfolane was used in place of dimethylsulfoxide. The electrolytic voltage was 5.7± during the reaction.
It showed a nearly constant value of 0.3V. Electrolytic fluorination reaction was carried out for 3200 hours. The reaction mixture was appropriately extracted from the bottom of the electrolytic cell. 6130 g of reaction mixture was obtained. The target product, perfluorotributylamine, is
Of that, 73% by weight (yield 35%) was present.
前記実施例と同じ手順で脱フツ化水素した後、
パーフルオロトリブチルアミンを蒸留で単離しよ
うとしたが、３−メチルスルホランのフツ素化物
と容易に分離することができなかつた。 After dehydrofluorination in the same procedure as in the above example,
An attempt was made to isolate perfluorotributylamine by distillation, but it could not be easily separated from the fluorinated product of 3-methylsulfolane.
実施例 ２
実施例１と同じ装置を使用し、トリブチルアミ
ンに代えてＮ−メチルパーヒドロイソキノリン
150ｇとジメチルスルホキシド６ｇを仕込み、電
流密度2.1A／ｄm2（電流8A）で電解フツ素化反
応を行つた。浴温は10〜15℃に保ち又電圧は5.5
〜6V示した。24時間毎にＮ−メチルパーヒドロ
イソキノリン23ｇ及びジメチルスルホキシド４ｇ
を添加した。電圧が9Vを越える迄合計960時間電
解が可能であつた。Example 2 Using the same equipment as in Example 1, N-methylperhydroisoquinoline was used instead of tributylamine.
150 g and 6 g of dimethyl sulfoxide were charged, and an electrolytic fluorination reaction was carried out at a current density of 2.1 A/dm 2 (current 8 A). Keep bath temperature at 10-15℃ and voltage at 5.5
It showed ~6V. 23 g N-methylperhydroisoquinoline and 4 g dimethyl sulfoxide every 24 hours
was added. Electrolysis was possible for a total of 960 hours until the voltage exceeded 9V.
下層を分液し2020ｇの粗製物を得た。これを実
施例１と同様に処理後精留し、沸点152〜154℃の
パーフルオロ−Ｎ−メチルパーヒドロイソキノリ
ン624ｇを得た。（収率18％）
なお、ジメチルスルホキサイドを添加しない場
合は90時間後で電圧9Vを越えた。 The lower layer was separated to obtain 2020 g of crude product. This was treated and then rectified in the same manner as in Example 1 to obtain 624 g of perfluoro-N-methylperhydroisoquinoline with a boiling point of 152 to 154°C. (Yield: 18%) Note that when dimethyl sulfoxide was not added, the voltage exceeded 9 V after 90 hours.
本発明の製法では、従来の添加剤の不飽和また
は飽和環状スルホン等に代えてジメチルスルホキ
シド等の低級アルキルスルホキシドを使用するの
で、電解フツ素化反応後、目的物と添加剤を分離
するのが容易である。また、低級アルキルスルホ
キシドは、従来の添加剤と同様、電極表面に樹脂
状物質が付着するのを防止する能力に優れたもの
である。
In the production method of the present invention, a lower alkyl sulfoxide such as dimethyl sulfoxide is used in place of the conventional additive such as unsaturated or saturated cyclic sulfone, so it is easy to separate the target product and the additive after the electrolytic fluorination reaction. It's easy. Further, lower alkyl sulfoxide, like conventional additives, has an excellent ability to prevent resinous substances from adhering to the electrode surface.
Claims (1)
あたり、式： Ｒ−SO−R′ （式中、ＲおよびR′は同一または相異なつて炭
素数１〜３の脂肪族基を示す。） で表される硫黄化合物を添加することを特徴とす
る電解フツ素化方法。 ２ 前記第三アミンが炭素数６〜18の脂肪族第三
アミンである特許請求の範囲第１項記載の電解フ
ツ素化方法。 ３ 前記硫黄化合物を前記第三アミン100重量部
に対し0.5〜30重量部添加する特許請求の範囲第
１項記載の電解フツ素化方法。[Claims] 1. In the electrolytic fluorination of a tertiary amine having 6 to 18 carbon atoms, the formula: R-SO-R' (wherein R and R' are the same or different and have 1 to 3 carbon atoms) An electrolytic fluorination method characterized by adding a sulfur compound represented by (representing an aliphatic group). 2. The electrolytic fluorination method according to claim 1, wherein the tertiary amine is an aliphatic tertiary amine having 6 to 18 carbon atoms. 3. The electrolytic fluorination method according to claim 1, wherein the sulfur compound is added in an amount of 0.5 to 30 parts by weight per 100 parts by weight of the tertiary amine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60272688A JPS62133094A (en) | 1985-12-04 | 1985-12-04 | Electrolytic fluorination method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60272688A JPS62133094A (en) | 1985-12-04 | 1985-12-04 | Electrolytic fluorination method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62133094A JPS62133094A (en) | 1987-06-16 |
| JPS6330399B2 true JPS6330399B2 (en) | 1988-06-17 |
Family
ID=17517407
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60272688A Granted JPS62133094A (en) | 1985-12-04 | 1985-12-04 | Electrolytic fluorination method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62133094A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01136198U (en) * | 1988-02-29 | 1989-09-18 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62224690A (en) * | 1986-03-26 | 1987-10-02 | Dainippon Ink & Chem Inc | Method for electrochemically fluorinating organic compound |
| JP2584825B2 (en) * | 1988-05-10 | 1997-02-26 | 株式会社トクヤマ | Electrolytic fluorination method |
-
1985
- 1985-12-04 JP JP60272688A patent/JPS62133094A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01136198U (en) * | 1988-02-29 | 1989-09-18 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62133094A (en) | 1987-06-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4714530A (en) | Method for producing high purity quaternary ammonium hydroxides | |
| US3899401A (en) | Electrochemical production of pinacols | |
| US4466881A (en) | Process for the preparation of (ω-fluorosulfonyl)haloaliphatic carboxylic acid fluorides | |
| US3274081A (en) | Electrochemical process for making fluorine-containing carbon compounds | |
| DE1595999A1 (en) | Process for the production of sulfonic acid halides and for their electrofluorination | |
| JPS6330399B2 (en) | ||
| US5366597A (en) | Process for the preparation of perfluorobutylsulphonyl fluoride | |
| US3951762A (en) | Preparation of perfluorinated organic sulfonyl fluorides | |
| US3692643A (en) | Electrofluorination process using thioesters | |
| US3423299A (en) | Electrochemical fluorination of polymethylene sulfones to produce perfluoroalkylsulfonyl fluorides | |
| US3193574A (en) | Process for the preparation of adiponitrile by dimerization of acrylonitrile | |
| US5326437A (en) | Process for production of perfluoroalkysulphonyl fluorides | |
| EP0638665B1 (en) | Process for the preparation of benzaldehyde dialkyl acetals | |
| US4298438A (en) | Preparation of 4-tert.-butylbenzaldehyde | |
| DE68905638T2 (en) | PRODUCTION OF ALKANSULFONYL HALIDES AND ALKANSULFONIC ACIDS. | |
| US6395165B2 (en) | Process for preparing perfluorinated organic compounds by electrochemical fluorination | |
| EP0711851B1 (en) | Process for manufacturing p-hydroxybenzaldehyde | |
| US3411997A (en) | Electrolytic process for preparing nlower acyloxymethyl-n-hydrocabyl lower acylamides and certain derivatives thereof | |
| JPS636633B2 (en) | ||
| US3453190A (en) | Electrochemical acyloxylation process | |
| DE1912738C3 (en) | Process for the preparation of perfluoroalkylsuHonyHIuorlden | |
| JP2008505953A (en) | Method for producing primary amines having a primary amino group and a cyclopropyl unit bonded to an aliphatic or alicyclic C-atom | |
| US4945168A (en) | Method of preparing aryl-(1-phthalimido)-alkyl ketones | |
| JPH02133590A (en) | Electrochemical synthesis of 2-aryl hydroquinone | |
| EP0525351A2 (en) | 2-Aryle-2,2-dialkoxyacetic acid alkyle esters, process for their preparation and use in the preparation of esters of aryle glyoxylic acid |