JPH0616656A - Production of fluorinated phthalic acid anhydride - Google Patents
Production of fluorinated phthalic acid anhydrideInfo
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- JPH0616656A JPH0616656A JP17545092A JP17545092A JPH0616656A JP H0616656 A JPH0616656 A JP H0616656A JP 17545092 A JP17545092 A JP 17545092A JP 17545092 A JP17545092 A JP 17545092A JP H0616656 A JPH0616656 A JP H0616656A
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- carbon atoms
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- chloride
- Prior art date
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Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は下記一般式（VII）：The present invention relates to the following general formula (VII):
【０００２】[0002]
【化１３】 [Chemical 13]
【０００３】（式中Ｒ1、及びＲ2は、それぞれ独立に、
フッ素原子、炭素原子数１〜１２個の直鎖アルコキシ
基、炭素原子数１〜１２個の分岐アルコキシ基、炭素原
子数１〜１２個のアルキルチオ基、炭素原子数１〜１２
個のアルキルアミノ基、アリールオキシ基、アリールチ
オ基、アリールアミノ基又は下記式（VIII）〜（XII）(Wherein R 1 and R 2 are, independently of each other,
Fluorine atom, straight-chain alkoxy group having 1 to 12 carbon atoms, branched alkoxy group having 1 to 12 carbon atoms, alkylthio group having 1 to 12 carbon atoms, 1 to 12 carbon atoms
Alkylamino group, aryloxy group, arylthio group, arylamino group or the following formulas (VIII) to (XII)
【０００４】[0004]
【化１４】 [Chemical 14]
【０００５】[0005]
【化１５】 [Chemical 15]
【０００６】[0006]
【化１６】 [Chemical 16]
【０００７】[0007]
【化１７】 [Chemical 17]
【０００８】[0008]
【化１８】 [Chemical 18]
【０００９】のいずれかを示す）で表される含フッ素無
水フタル酸類の製造方法に関する。The method for producing the fluorine-containing phthalic anhydrides represented by
【００１０】本発明にかかる含フッ素無水フタル酸類
は、医薬、農薬、光学材料、配線基盤材料、感光材料、
液晶材料等の中間原料として有用である。The fluorine-containing phthalic anhydrides according to the present invention are used as medicines, agricultural chemicals, optical materials, wiring board materials, photosensitive materials,
It is useful as an intermediate raw material for liquid crystal materials.
【００１１】[0011]
【従来の技術】含フッ素無水フタル酸類の合成方法とし
ては、例えば、英国特許番号第９８６８９２号公報など
に、下記スキーム（Ａ）に示すように、テトラフルオロ
フタル酸を無水トリフルオロ酢酸により脱水する方法が
記載されている。As a method for synthesizing fluorine-containing phthalic anhydrides, for example, tetrafluorophthalic acid is dehydrated with trifluoroacetic anhydride as shown in the following scheme (A) in British Patent No. 986892. The method is described.
【００１２】[0012]
【化１９】 [Chemical 19]
【００１３】しかしながら、この方法において使用する
無水トリフルオロ酢酸は、高価であるうえに副生するト
リフルオロ酢酸が腐食性の強い物質であるという問題点
があり、工業的に実施するのは困難である。However, the trifluoroacetic anhydride used in this method has the problems that it is expensive and that trifluoroacetic acid, which is a by-product, is a highly corrosive substance, and it is difficult to carry out it industrially. is there.
【００１４】また、特開平２−３０６９４５号公報に
は、トルエン、キシレン等不活性な有機溶媒の存在下に
加熱脱水する方法が記載されている。しかしながら、こ
の方法は目的とする無水フタル酸類の収率が低いという
欠点を有している。Further, Japanese Patent Laid-Open No. 2-306945 describes a method of heating and dehydrating in the presence of an inert organic solvent such as toluene and xylene. However, this method has the drawback that the yield of the desired phthalic anhydrides is low.
【００１５】[0015]
【発明が解決しようとする課題】本発明は従来技術の有
する前記事情に鑑みてなされたものである。すなわち、
本発明の目的は、含フッ素フタル酸類から該含フッ素フ
タル酸無水物を安全に収率よく製造でき、しかも純度よ
く製造する方法を提供することにある。SUMMARY OF THE INVENTION The present invention has been made in view of the above circumstances of the prior art. That is,
An object of the present invention is to provide a method for producing the fluorinated phthalic anhydride from the fluorinated phthalic acids safely and in a high yield, and also for producing the phthalic anhydride in high purity.
【００１６】[0016]
【課題を解決するための手段】本発明によれば、下記一
般式（I）：According to the present invention, the following general formula (I):
【００１７】[0017]
【化２０】 [Chemical 20]
【００１８】（式中Ｒ1、及びＲ2は、それぞれ独立に、
フッ素原子、炭素原子数１〜１２個の直鎖アルコキシ
基、炭素原子数１〜１２個の分岐アルコキシ基、炭素原
子数１〜１２個のアルキルチオ基、炭素原子数１〜１２
個のアルキルアミノ基、アリールオキシ基、アリールチ
オ基、アリールアミノ基又は下記式（II）〜（VI）(In the formula, R 1 and R 2 are each independently
Fluorine atom, straight-chain alkoxy group having 1 to 12 carbon atoms, branched alkoxy group having 1 to 12 carbon atoms, alkylthio group having 1 to 12 carbon atoms, 1 to 12 carbon atoms
Alkylamino group, aryloxy group, arylthio group, arylamino group or the following formulas (II) to (VI)
【００１９】[0019]
【化２１】 [Chemical 21]
【００２０】[0020]
【化２２】 [Chemical formula 22]
【００２１】[0021]
【化２３】 [Chemical formula 23]
【００２２】[0022]
【化２４】 [Chemical formula 24]
【００２３】[0023]
【化２５】 [Chemical 25]
【００２４】のいずれかを示す）で表される含フッ素フ
タル酸類を塩化チオニル、塩化アセチルおよび塩化ホス
ホリルからなる群から選択される少なくとも１種の溶媒
中４０〜１０５℃で加熱処理することを特徴とする下記
一般式（VII）：Fluorine-containing phthalic acid represented by any one of (1) to (4) is heat treated at 40 to 105 ° C. in at least one solvent selected from the group consisting of thionyl chloride, acetyl chloride and phosphoryl chloride. And the following general formula (VII):
【００２５】[0025]
【化２６】 [Chemical formula 26]
【００２６】（式中Ｒ1、及びＲ2は、それぞれ独立に、
フッ素原子、炭素原子数１〜１２個の直鎖アルコキシ
基、炭素原子数１〜１２個の分岐アルコキシ基、炭素原
子数１〜１２個のアルキルチオ基、炭素原子数１〜１２
個のアルキルアミノ基、アリールオキシ基、アリールチ
オ基、アリールアミノ基又は下記式（VIII）〜（XII）(Wherein R 1 and R 2 are each independently
Fluorine atom, straight-chain alkoxy group having 1 to 12 carbon atoms, branched alkoxy group having 1 to 12 carbon atoms, alkylthio group having 1 to 12 carbon atoms, 1 to 12 carbon atoms
Alkylamino group, aryloxy group, arylthio group, arylamino group or the following formulas (VIII) to (XII)
【００２７】[0027]
【化２７】 [Chemical 27]
【００２８】[0028]
【化２８】 [Chemical 28]
【００２９】[0029]
【化２９】 [Chemical 29]
【００３０】[0030]
【化３０】 [Chemical 30]
【００３１】[0031]
【化３１】 [Chemical 31]
【００３２】のいずれかを示す）で表される含フッ素無
水フタル酸類の製造方法が提供される。A method for producing a fluorine-containing phthalic anhydride represented by any of (1) to (3) is provided.
【００３３】[0033]
【発明の具体的な説明】以下に、本願発明について具体
的に説明する。DETAILED DESCRIPTION OF THE INVENTION The present invention will be specifically described below.
【００３４】本発明における出発原料である上記一般式
（I）で表される含フッ素フタル酸類を具体的に示す
と、３，４，５，６−テトラフルオロフタル酸、４−ブ
トキシ−３，５，６−トリフルオロフタル酸、４−メト
キシ−３，５，６−トリフルオロフタル酸、４−フェノ
キシ−３，５，６−トリフルオロフタル酸、４−オクチ
ルオキシ−３，５，６−トリフルオロフタル酸、４−ド
デシルオキシ−３，５，６−トリフルオロフタル酸、４
−フェニルアミノ−３，５，６−トリフルオロフタル
酸、４−フェニルチオ−３，５，６−トリフルオロフタ
ル酸、４，５−ジドデシルチオ−３，６−ジフルオロフ
タル酸、４，５−ジメトキシ−３，６−ジフルオロフタ
ル酸、４，５−ジブチルアミノ−３，６−ジフルオロフ
タル酸、４，５−ジフェノキシ−３，６−ジフルオロフ
タル酸、４，５−ジフェニルアミノ−３，６−ジフルオ
ロフタル酸、４，５−ジブチルチオ−３，６−ジフルオ
ロフタル酸、４，５−ジオクチルチオ−３，６−ジフル
オロフタル酸、４−フェノキシ−５−フェニルチオ−
３，６−ジフルオロフタル酸、４−フェノキシ−５−ブ
トキシ−３，６−ジフルオロフタル酸、４−ブトキシ−
５−ブチルチオ−３，６−ジフルオロフタル酸、１，４
−ビス（３，４−ジカルボキシ−２，５，６−トリフル
オロフェノキシ）テトラフルオロベンゼン、１，４−ビ
ス（３，４−ジカルボキシ−２，５，６−トリフルオロ
フェニルチオ）テトラフルオロベンゼン、４，４´−ビ
ス（３，４−ジカルボキシ−２，５，６−トリフルオロ
フェノキシ）オクタフルオロビフェニル、４，４´−ビ
ス（３，４−ジカルボキシ−２，５，６−トリフルオロ
フェニルチオ）オクタフルオロビフェニル、ビス（３，
５，６−トリフルオロフタル酸）オキシド、ビス（３，
５，６−トリフルオロフタル酸）スルフィドなどが挙げ
られる。Specific examples of the fluorine-containing phthalic acids represented by the above general formula (I), which are the starting materials in the present invention, are 3,4,5,6-tetrafluorophthalic acid, 4-butoxy-3, 5,6-Trifluorophthalic acid, 4-methoxy-3,5,6-trifluorophthalic acid, 4-phenoxy-3,5,6-trifluorophthalic acid, 4-octyloxy-3,5,6- Trifluorophthalic acid, 4-dodecyloxy-3,5,6-trifluorophthalic acid, 4
-Phenylamino-3,5,6-trifluorophthalic acid, 4-phenylthio-3,5,6-trifluorophthalic acid, 4,5-didodecylthio-3,6-difluorophthalic acid, 4,5-dimethoxy- 3,6-difluorophthalic acid, 4,5-dibutylamino-3,6-difluorophthalic acid, 4,5-diphenoxy-3,6-difluorophthalic acid, 4,5-diphenylamino-3,6-difluorophthalic acid Acid, 4,5-dibutylthio-3,6-difluorophthalic acid, 4,5-dioctylthio-3,6-difluorophthalic acid, 4-phenoxy-5-phenylthio-
3,6-difluorophthalic acid, 4-phenoxy-5-butoxy-3,6-difluorophthalic acid, 4-butoxy-
5-Butylthio-3,6-difluorophthalic acid, 1,4
-Bis (3,4-dicarboxy-2,5,6-trifluorophenoxy) tetrafluorobenzene, 1,4-bis (3,4-dicarboxy-2,5,6-trifluorophenylthio) tetrafluoro Benzene, 4,4'-bis (3,4-dicarboxy-2,5,6-trifluorophenoxy) octafluorobiphenyl, 4,4'-bis (3,4-dicarboxy-2,5,6- Trifluorophenylthio) octafluorobiphenyl, bis (3,3
5,6-trifluorophthalic acid) oxide, bis (3,3
5,6-trifluorophthalic acid) sulfide and the like.
【００３５】本発明においては、溶媒として塩化チオニ
ル、塩化アセチル及び塩化ホスホリルからなる群から選
択される少なくとも１種を用いるが、特に塩化チオニル
及び／又は塩化アセチルを用いるのが好ましい。In the present invention, at least one selected from the group consisting of thionyl chloride, acetyl chloride and phosphoryl chloride is used as the solvent, but thionyl chloride and / or acetyl chloride are particularly preferably used.
【００３６】含フッ素フタル酸類化合物の溶媒中での濃
度は、３重量％以上６０重量％以下で使用するのが好ま
しく、特に５重量％以上３０重量％以下で使用するのが
好ましい。The concentration of the fluorine-containing phthalic acid compound in the solvent is preferably 3% by weight or more and 60% by weight or less, and more preferably 5% by weight or more and 30% by weight or less.
【００３７】反応温度は４０〜１０５℃の範囲であり、
特に、塩化チオニルを用いる場合５０〜８０℃が好まし
く、塩化アセチルを用いる場合４０〜５０℃が好まし
く、塩化ホスホリルを用いた場合８０〜１０５℃の範囲
が好ましい。反応温度が１０５℃を越える高温度である
場合には、カルボン酸クロライドが副生成するので好ま
しくない。また、４０℃未満の低温度で行った場合には
生産効率が低下するので好ましくない。The reaction temperature is in the range of 40 to 105 ° C,
Particularly, when thionyl chloride is used, the temperature is preferably 50 to 80 ° C., when acetyl chloride is used, it is preferably 40 to 50 ° C., and when phosphoryl chloride is used, the temperature is preferably 80 to 105 ° C. If the reaction temperature is higher than 105 ° C., carboxylic acid chloride is by-produced, which is not preferable. Further, if the temperature is lower than 40 ° C., the production efficiency is lowered, which is not preferable.
【００３８】反応時間は、使用する溶媒、反応温度など
により異なるが、通常１〜４時間の範囲で行うのが望ま
しい。The reaction time varies depending on the solvent used, the reaction temperature, etc., but it is usually desirable to carry out the reaction in the range of 1 to 4 hours.
【００３９】反応終了後は、例えば、溶媒として塩化チ
オニル、塩化アセチルを用いた場合には、反応溶媒を留
去することにより、上記一般式（VII）で示される含フ
ッ素無水フタル酸類化合物を得ることができる。また、
例えば、溶媒として塩化ホスホリルを用いた場合には、
反応溶媒を留去した後、生成物をイソプロピルエーテル
などの有機溶媒に溶解させ、濾過によりリン酸を濾別
し、濾液を蒸発乾固することにより、上記一般式（VI
I）で示される含フッ素無水フタル酸類化合物を得るこ
とができる。After completion of the reaction, for example, when thionyl chloride or acetyl chloride is used as a solvent, the reaction solvent is distilled off to obtain a fluorine-containing phthalic anhydride compound represented by the above general formula (VII). be able to. Also,
For example, when phosphoryl chloride is used as the solvent,
After distilling off the reaction solvent, the product was dissolved in an organic solvent such as isopropyl ether, phosphoric acid was filtered off by filtration, and the filtrate was evaporated to dryness to give the above-mentioned general formula (VI
A fluorinated phthalic anhydride compound represented by I) can be obtained.
【００４０】[0040]
【発明の効果】本発明の製造方法によれば、含フッ素フ
タル酸類から該含フッ素フタル酸無水物を安全に収率よ
く製造でき、しかも純度よく製造することができる。According to the production method of the present invention, the fluorine-containing phthalic anhydride can be produced safely from the fluorine-containing phthalic acids in a high yield and can be produced in a high purity.
【００４１】以下、本発明を実施例により更に具体的に
説明する。Hereinafter, the present invention will be described more specifically by way of examples.
【００４２】[0042]
【実施例】実施例１ 冷却還流管、温度計及び滴下ロートを備えた100mlの四
ツ口フラスコ中に、テトラフルオロフタル酸30.0ｇ（0.
13mol）を加えた後、滴下ロートより塩化チオニル70.0
ｇ（0.59mol）を加えた。その後70℃で約3時間反応させ
た。反応終了後、塩化チオニルを減圧下留去し、得られ
た結晶を更に60℃にて減圧乾燥することにより、テトラ
フルオロ無水フタル酸26.9g(0.12mol)を得た（対含フッ
素フタル酸収率97mol%）。得られたテトラフルオロ無水
フタル酸の物性値は次の通りである。 Example 1 In a 100 ml four-necked flask equipped with a cooling reflux tube, a thermometer and a dropping funnel, 30.0 g of tetrafluorophthalic acid (0.
13 mol), and then thionyl chloride 70.0 from the dropping funnel.
g (0.59 mol) was added. Then, the mixture was reacted at 70 ° C for about 3 hours. After the reaction was completed, thionyl chloride was distilled off under reduced pressure, and the obtained crystals were further dried under reduced pressure at 60 ° C. to obtain 26.9 g (0.12 mol) of tetrafluorophthalic anhydride (compared with phthalic acid containing fluorine). Rate 97 mol%). The physical properties of the obtained tetrafluorophthalic anhydride are as follows.
【００４３】 実施例２ 実施例１と同様の装置を用い、テトラフルオロフタル酸
30.0g(0.13mol)を加えた後、滴下ロートより塩化アセチ
ル70g(0.9mol)を加える。その後50℃で約4時間反応させ
た。反応終了後塩化アセチルを減圧下留去し、得られた
結晶をさらに60℃にて乾燥することにより、テトラフル
オロ無水フタル酸25.7g(0.12mol)を得た（対含フッ素フ
タル酸収率93mol%）。[0043] Example 2 Using the same apparatus as in Example 1, tetrafluorophthalic acid
After adding 30.0 g (0.13 mol), 70 g (0.9 mol) of acetyl chloride is added from a dropping funnel. Then, the mixture was reacted at 50 ° C for about 4 hours. After completion of the reaction, acetyl chloride was distilled off under reduced pressure, and the obtained crystals were further dried at 60 ° C. to obtain 25.7 g (0.12 mol) of tetrafluorophthalic anhydride (yield of fluorine-containing phthalic acid: 93 mol %).
【００４４】実施例３ 実施例１と同様の装置を用い、テトラフルオロフタル酸
30.0g(0.13mol)を加えた後、滴下ロートより塩化ホスホ
リル70g(0.46mol)を加える。その後100℃で約1時間反応
させた。反応終了後塩化ホスホリルを減圧下留去した
後、生成物をジイソプロピルエーテルに溶解させろ過に
よりリン酸を除去した。その後減圧下ジイソプロピルエ
ーテルを留去し、得られた結晶をさらに60℃にて減圧乾
燥することにより、テトラフルオロ無水フタル酸26.0g
(0.12mol)を得た（対含フッ素フタル酸収率94mol%）。 Example 3 Using the same apparatus as in Example 1, tetrafluorophthalic acid
After adding 30.0 g (0.13 mol), 70 g (0.46 mol) of phosphoryl chloride is added from a dropping funnel. Then, the mixture was reacted at 100 ° C for about 1 hour. After completion of the reaction, phosphoryl chloride was distilled off under reduced pressure, the product was dissolved in diisopropyl ether, and phosphoric acid was removed by filtration. Then, diisopropyl ether was distilled off under reduced pressure, and the resulting crystals were further dried under reduced pressure at 60 ° C. to give 26.0 g of tetrafluorophthalic anhydride.
(0.12 mol) was obtained (yield of 94% by mol of fluorine-containing phthalic acid).
【００４５】実施例４〜１０ 実施例１と同様の装置を用い、各種含フッ素フタル酸を
用い、表１に示す該含フッ素フタル酸の仕込量、溶媒量
を用いた以外は、実施例１と同様の方法で行うことによ
って、表１に示す収率の該含フッ素無水フタル酸を得
た。 Examples 4 to 10 Example 1 was repeated, except that various fluorine-containing phthalic acids were used in the same apparatus as in Example 1 except that the amount of fluorine-containing phthalic acid and the amount of solvent shown in Table 1 were used. The same procedure as in (1) above was performed to obtain the fluorine-containing phthalic anhydride in the yields shown in Table 1.
【００４６】実施例１１〜１５ 実施例１と同様の装置を用い、各種含フッ素フタル酸を
用い、表２に示す該含フッ素フタル酸の仕込量、溶媒量
を用いた以外は、実施例２と同様の方法で行うことによ
って、表２に示す収率の該含フッ素無水フタル酸を得
た。 Examples 11 to 15 Example 2 was repeated except that the same apparatus as in Example 1 was used, various kinds of fluorine-containing phthalic acid were used, and the amounts of fluorine-containing phthalic acid and solvent shown in Table 2 were used. By performing the same method as described above, the fluorine-containing phthalic anhydride having the yield shown in Table 2 was obtained.
【００４７】実施例１６〜２０ 実施例１と同様の装置を用い、各種含フッ素フタル酸を
用い、表３に示す該含フッ素フタル酸の仕込量、溶媒量
を用いた以外は、実施例３と同様の方法で行うことによ
って、表３に示す収率の該含フッ素無水フタル酸を得
た。 Examples 16 to 20 Example 3 was repeated except that the same apparatus as in Example 1 was used, various fluorinated phthalic acids were used, and the amounts of fluorinated phthalic acid and solvent shown in Table 3 were used. The fluorine-containing phthalic anhydride having the yields shown in Table 3 was obtained by the same method as described above.
【００４８】実施例２１ 冷却還流管、温度計及び滴下ロートを備えた300ml四ツ
口フラスコに1,4-ビス(3,4-ジカルボキシ-2,5,6-トリフ
ルオロフェノキシ)テトラフルオロベンゼン10g(0.016mo
l)を加えた後、滴下ロートより塩化チオニル200g(1.72m
ol)を加えた。その後70℃で約4時間反応させた。反応終
了後塩化チオニルを減圧下留去し、得られた結晶を更に
60℃にて減圧乾燥することにより、上記の酸無水物9.0g
(0.016mol)を得た（対フタル酸収率98mol%）。得られた
化合物を昇華精製したものについての物性値は次の通り
である。 Example 21 1,4-bis (3,4-dicarboxy-2,5,6-trifluorophenoxy) tetrafluorobenzene was placed in a 300 ml four-necked flask equipped with a cooling reflux tube, a thermometer and a dropping funnel. 10g (0.016mo
l) was added, and then 200 g (1.72 m) of thionyl chloride was added from the dropping funnel.
ol) was added. Then, the mixture was reacted at 70 ° C for about 4 hours. After the reaction was completed, thionyl chloride was distilled off under reduced pressure, and the obtained crystals were further
By drying under reduced pressure at 60 ℃, 9.0g of the above acid anhydride
(0.016 mol) was obtained (yield to phthalic acid: 98 mol%). The physical properties of the obtained compound obtained by sublimation purification are as follows.
【００４９】 実施例２２〜２７ 実施例２１と同様の装置を用い、各種含フッ素フタル酸
を用い、表４に示す該含フッ素フタル酸の仕込量、溶媒
量を用いた以外は、実施例２１と同様の方法で行うこと
によって、表４に示す収率の該含フッ素無水フタル酸を
得た。[0049] Examples 22 to 27 The same apparatus as in Example 21 was used, except that various fluorine-containing phthalic acids were used, and the amount of fluorine-containing phthalic acid and the amount of solvent shown in Table 4 were used. By the method, the fluorine-containing phthalic anhydride having the yield shown in Table 4 was obtained.
【００５０】[0050]
【表１】 [Table 1]
【００５１】[0051]
【表２】 [Table 2]
【００５２】[0052]
【表３】 [Table 3]
【００５３】[0053]
【表４】 [Table 4]
Claims (1)
炭素原子数１〜１２個の直鎖アルコキシ基、炭素原子数
１〜１２個の分岐アルコキシ基、炭素原子数１〜１２個
のアルキルチオ基、炭素原子数１〜１２個のアルキルア
ミノ基、アリールオキシ基、アリールチオ基、アリール
アミノ基又は下記式（II）〜（VI） 【化２】 【化３】 【化４】 【化５】 【化６】 のいずれかを示す）で表される含フッ素フタル酸類を塩
化チオニル、塩化アセチルおよび塩化ホスホリルからな
る群から選択される少なくとも１種の溶媒中４０〜１０
５℃で加熱処理することを特徴とする下記一般式（VI
I）： 【化７】 （式中Ｒ1、及びＲ2は、それぞれ独立に、フッ素原子、
炭素原子数１〜１２個の直鎖アルコキシ基、炭素原子数
１〜１２個の分岐アルコキシ基、炭素原子数１〜１２個
のアルキルチオ基、炭素原子数１〜１２個のアルキルア
ミノ基、アリールオキシ基、アリールチオ基、アリール
アミノ基又は下記式（VIII）〜（XII） 【化８】 【化９】 【化１０】 【化１１】 【化１２】 のいずれかを示す）で表される含フッ素無水フタル酸類
の製造方法。1. The following general formula (I): (In the formula, R 1 and R 2 are each independently a fluorine atom,
Linear alkoxy group having 1 to 12 carbon atoms, branched alkoxy group having 1 to 12 carbon atoms, alkylthio group having 1 to 12 carbon atoms, alkylamino group having 1 to 12 carbon atoms, aryloxy Group, arylthio group, arylamino group or the following formulas (II) to (VI): [Chemical 3] [Chemical 4] [Chemical 5] [Chemical 6] 40 to 10 in a solvent of at least one selected from the group consisting of thionyl chloride, acetyl chloride and phosphoryl chloride.
The following general formula (VI
I): [Chemical 7] (In the formula, R 1 and R 2 are each independently a fluorine atom,
Linear alkoxy group having 1 to 12 carbon atoms, branched alkoxy group having 1 to 12 carbon atoms, alkylthio group having 1 to 12 carbon atoms, alkylamino group having 1 to 12 carbon atoms, aryloxy Group, arylthio group, arylamino group or the following formulas (VIII) to (XII) [Chemical 9] [Chemical 10] [Chemical 11] [Chemical 12] The method for producing the fluorinated phthalic anhydrides represented by
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| JP04175450A JP3130653B2 (en) | 1992-07-02 | 1992-07-02 | Method for producing fluorinated phthalic anhydrides |
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| JP04175450A JP3130653B2 (en) | 1992-07-02 | 1992-07-02 | Method for producing fluorinated phthalic anhydrides |
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| JP (1) | JP3130653B2 (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995010502A1 (en) * | 1993-10-12 | 1995-04-20 | Nippon Shokubai Co., Ltd. | Process for producing 3-substituted 2,4,5-trifluorobenzoic acid, and 4-amino-3,5,6-trifluorophthalic acid |
| US5488152A (en) * | 1994-02-12 | 1996-01-30 | Hoechst Aktiengesellschaft | Process for the preparation of 4-alkoxy-3,5,6-trifluoro-phthalic acids and 3-alkoxy-2,4,5-trifluorobenzoic acids |
| WO2002079181A1 (en) * | 2001-03-29 | 2002-10-10 | Bayer Aktiengesellschaft | Benzofuran derivatives |
| US6916959B2 (en) | 2001-05-11 | 2005-07-12 | Nippon Shokubai Co., Ltd. | Halogen-containing aromatic compound |
| WO2010134630A1 (en) | 2009-05-21 | 2010-11-25 | 住友化学株式会社 | Production method of halogen-substituted phthalide |
| CN103242860A (en) * | 2013-05-15 | 2013-08-14 | 江苏和成显示科技股份有限公司 | Liquid crystal composition and liquid crystal display device |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004111026A1 (en) | 2003-06-17 | 2004-12-23 | Nippon Shokubai Co., Ltd. | Bis (fluorine-containing phthalic anhydride) and method for production thereof |
| GB0823719D0 (en) | 2008-12-31 | 2009-02-04 | Spd Swiss Prec Diagnostics Gmb | A conductive measurement cell |
-
1992
- 1992-07-02 JP JP04175450A patent/JP3130653B2/en not_active Expired - Fee Related
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995010502A1 (en) * | 1993-10-12 | 1995-04-20 | Nippon Shokubai Co., Ltd. | Process for producing 3-substituted 2,4,5-trifluorobenzoic acid, and 4-amino-3,5,6-trifluorophthalic acid |
| GB2289048A (en) * | 1993-10-12 | 1995-11-08 | Nippon Catalytic Chem Ind | Process for producing 3-substituted 2,4,5-trifluorobenzoic acid,and 4-amino-3,5,6-trifluorophthalic acid |
| US5488152A (en) * | 1994-02-12 | 1996-01-30 | Hoechst Aktiengesellschaft | Process for the preparation of 4-alkoxy-3,5,6-trifluoro-phthalic acids and 3-alkoxy-2,4,5-trifluorobenzoic acids |
| WO2002079181A1 (en) * | 2001-03-29 | 2002-10-10 | Bayer Aktiengesellschaft | Benzofuran derivatives |
| US6916959B2 (en) | 2001-05-11 | 2005-07-12 | Nippon Shokubai Co., Ltd. | Halogen-containing aromatic compound |
| US7217827B2 (en) | 2001-05-11 | 2007-05-15 | Nippon Shokubai Co., Ltd. | Halogen-containing aromatic compound |
| WO2010134630A1 (en) | 2009-05-21 | 2010-11-25 | 住友化学株式会社 | Production method of halogen-substituted phthalide |
| CN103242860A (en) * | 2013-05-15 | 2013-08-14 | 江苏和成显示科技股份有限公司 | Liquid crystal composition and liquid crystal display device |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3130653B2 (en) | 2001-01-31 |
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