JPH0235744B2 - - Google Patents
Info
- Publication number
- JPH0235744B2 JPH0235744B2 JP57109965A JP10996582A JPH0235744B2 JP H0235744 B2 JPH0235744 B2 JP H0235744B2 JP 57109965 A JP57109965 A JP 57109965A JP 10996582 A JP10996582 A JP 10996582A JP H0235744 B2 JPH0235744 B2 JP H0235744B2
- Authority
- JP
- Japan
- Prior art keywords
- carbonate
- bis
- trifluoromethylphenyl
- chloro
- parts
- 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
- JFQUVGSOOYKCAH-UHFFFAOYSA-N bis[4-(trifluoromethyl)phenyl] carbonate Chemical compound C1=CC(C(F)(F)F)=CC=C1OC(=O)OC1=CC=C(C(F)(F)F)C=C1 JFQUVGSOOYKCAH-UHFFFAOYSA-N 0.000 claims description 10
- -1 2-chloro-4-trifluoromethylphenyl Chemical group 0.000 claims description 9
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 7
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 7
- 239000011968 lewis acid catalyst Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 4
- UOULCEYHQNCFFH-UHFFFAOYSA-M sodium;hydroxymethanesulfonate Chemical compound [Na+].OCS([O-])(=O)=O UOULCEYHQNCFFH-UHFFFAOYSA-M 0.000 claims description 2
- GOFURTAJNOZTTO-UHFFFAOYSA-N bis[2-chloro-4-(trifluoromethyl)phenyl] carbonate Chemical compound ClC1=CC(C(F)(F)F)=CC=C1OC(=O)OC1=CC=C(C(F)(F)F)C=C1Cl GOFURTAJNOZTTO-UHFFFAOYSA-N 0.000 description 7
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 3
- AQJFATAFTQCRGC-UHFFFAOYSA-N 2-Chloro-4-methylphenol Chemical compound CC1=CC=C(O)C(Cl)=C1 AQJFATAFTQCRGC-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 229910018287 SbF 5 Inorganic materials 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- YPRIWFGTVJWQAM-UHFFFAOYSA-N bis[4-(trichloromethyl)phenyl] carbonate Chemical compound C1=CC(C(Cl)(Cl)Cl)=CC=C1OC(=O)OC1=CC=C(C(Cl)(Cl)Cl)C=C1 YPRIWFGTVJWQAM-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- BNIXVQGCZULYKV-UHFFFAOYSA-N pentachloroethane Chemical compound ClC(Cl)C(Cl)(Cl)Cl BNIXVQGCZULYKV-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000005406 washing Methods 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明は、ビス（４−トリフルオロメチルフエ
ニル）カーボネートの２位を選択的に核塩素化す
ることによつて、ビス（２−クロロ−４−トリフ
ルオロメチルフエニル）カーボネートを製造する
新規な方法に関する。Detailed Description of the Invention The present invention provides bis(2-chloro-4-trifluoromethylphenyl) carbonate by selectively nuclear chlorinating the 2-position of bis(4-trifluoromethylphenyl) carbonate. The present invention relates to a novel method for producing enyl) carbonate.
ビス（２−クロロ−４−トリフルオロメチルフ
エニル）カーボネートは、医薬、染料および最近
特に農薬の製造原料として注目されている有用な
化合物である。 Bis(2-chloro-4-trifluoromethylphenyl) carbonate is a useful compound that has recently attracted attention as a raw material for the production of pharmaceuticals, dyes, and especially agricultural chemicals.
従来、ビス（２−クロロ−４−トリフルオロメ
チルフエニル）カーボネートの合成法としては、
ドイツ特許1257784号公報に、トリフルオロメチ
ルフエノール類製造の前駆体として、ビス（２−
クロロ−４−トリクロロメチルフエニル）カーボ
ネートを無水フツ化水素酸（以下HEと略称）と
反応させ、ビス（２−クロロ−４−トリフルオロ
フエニル）カーボネートを得る方法が記載されて
いる。 Conventionally, the synthesis method for bis(2-chloro-4-trifluoromethylphenyl) carbonate is as follows:
German Patent No. 1257784 describes bis(2-
A method is described in which chloro-4-trichloromethylphenyl) carbonate is reacted with hydrofluoric anhydride (hereinafter abbreviated as HE) to obtain bis(2-chloro-4-trifluorophenyl) carbonate.
しかしこの方法は、出発原料となるビス（２−
クロロ−４−トリクロロメチルフエニル）カーボ
ネートを得るための２−クロロ−４−メチルフエ
ノールは工業的に入手が不可能な現状である。 However, this method uses bis(2-
Currently, 2-chloro-4-methylphenol for obtaining chloro-4-trichloromethylphenyl) carbonate is not available industrially.
直接核塩素化反応によつてビス（２−クロロ−
４−トリフルオロメチルフエニル）カーボネート
を得る方法についてはこれまで全く報告されてい
ない。 Bis(2-chloro-
No method for obtaining 4-trifluoromethylphenyl) carbonate has been reported so far.
本発明者等はこうした現状に鑑み工業化可能な
製造法を見い出すべく種々検討した結果、驚くべ
きことに、ビス（４−トリフルオロメチルフエニ
ル）カーボネートを核塩素化することにより、異
性体および塩素置換数の異なる副生成物を殆んど
生成させずに、選択的にベンゼン核の２位に、塩
素置換したビス（２−クロロ−４−トリフルオロ
メチルフエニル）カーボネートが、収率95％以上
高収率、純度95％以上の高純度で得られることを
見い出し本発明を完成した。 In view of the current situation, the present inventors conducted various studies to find a production method that can be industrialized, and surprisingly, by nuclear chlorination of bis(4-trifluoromethylphenyl) carbonate, isomers and chlorine Bis(2-chloro-4-trifluoromethylphenyl) carbonate, which is selectively substituted with chlorine at the 2-position of the benzene nucleus, is produced in a yield of 95%, with almost no by-products having different numbers of substitutions. The present invention has been completed by discovering that it can be obtained in high yield and with high purity of 95% or more.
すなわち本発明は、ビス（４−トリフルオロメ
チルフエニル）カーボネートを不活性有機溶剤に
溶解し、ルイス酸触媒存在下に塩素ガスと反応さ
せ、選択的にビス（２−クロロ−４−トリフルオ
ロメチルフエニル）カーボネートを得ることを特
徴とするビス（２−クロロ−４−トリフルオロメ
チルフエニル）カーボネートの製造法である。 That is, in the present invention, bis(4-trifluoromethylphenyl) carbonate is dissolved in an inert organic solvent and reacted with chlorine gas in the presence of a Lewis acid catalyst to selectively produce bis(2-chloro-4-trifluoromethylphenyl). This is a method for producing bis(2-chloro-4-trifluoromethylphenyl) carbonate, which is characterized by obtaining methylphenyl) carbonate.
本発明の出発原料であるビス（４−トリフルオ
ロメチルフエニル）カーボネートは、４−メチル
フエノールをホスゲンまたはトリクロロメチルク
ロロホーメートと反応させ、ビス（４−メチルフ
エニル）カーボネートとし、次いで側鎖塩素化
し、得られたビス（４−トリクロロメチルフエニ
ル）カーボネートとHFでフツ素化する通常の方
法で容易に高収率で得ることが出来る。 Bis(4-trifluoromethylphenyl) carbonate, which is the starting material of the present invention, is obtained by reacting 4-methylphenol with phosgene or trichloromethyl chloroformate to form bis(4-methylphenyl) carbonate, and then chlorinating the side chain. can be easily obtained in high yield by the usual method of fluorinating the obtained bis(4-trichloromethylphenyl) carbonate with HF.
本発明に使用される不活性有機溶媒としては、
例えば四塩化炭素、１，１，１−トリクロロエタ
ン、１，１，２，２−テトラクロロエタン、ペン
タクロロエタン、ブロモホルユ、１，２−ジブロ
モエタン、ニトロベンゼンなどがあげられる。 Inert organic solvents used in the present invention include:
Examples include carbon tetrachloride, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, pentachloroethane, bromoforu, 1,2-dibromoethane, and nitrobenzene.
不活性有機溶剤の量はビス（４−トリフルオロ
メチルフエニル）カーボネートを溶解し、均一系
で反応を進めることができる量の２〜20重量部が
用いられる。 The amount of inert organic solvent used is 2 to 20 parts by weight, which is sufficient to dissolve bis(4-trifluoromethylphenyl) carbonate and allow the reaction to proceed in a homogeneous system.
ビス（４−トリフルオロメチルフエニル）カー
ボネートは上記溶媒に溶解させ、次いでルイス酸
触媒を添加し、この混合液中に塩素ガスを導入し
て反応を行なうが、ルイス酸触媒としては例え
ば、AlCl3、FeCl3、SbCl3、SbCl5、SnCl4、
TaCl5、NdCl5、MoCl5、MoF5、SbF5などがあ
げられる。 Bis(4-trifluoromethylphenyl) carbonate is dissolved in the above solvent, then a Lewis acid catalyst is added, and chlorine gas is introduced into the mixture to carry out the reaction. As the Lewis acid catalyst, for example, AlCl 3 , FeCl3 , SbCl3 , SbCl5 , SnCl4 ,
Examples include TaCl 5 , NdCl 5 , MoCl 5 , MoF 5 and SbF 5 .
上記ルイス酸触媒の添加量はビス（４−トリフ
ルオロメチルフエニル）カーボネートに対して
0.1〜５重量％、好ましくは0.5〜1.5％である。ル
イス酸触媒の添加は分割または一括して添加する
ことができる。 The amount of Lewis acid catalyst added is based on bis(4-trifluoromethylphenyl) carbonate.
0.1-5% by weight, preferably 0.5-1.5%. The Lewis acid catalyst can be added in portions or all at once.
反応温度は30〜150℃、好ましくは70〜110℃で
ある。塩素ガス導入速度は、この温度を保つよう
塩素ガスの逸散をおさえることができる範囲で調
節される。その導入量は、ビス（４−トリフルオ
ロメチルフエニル）カーボネート１モルに対して
反応にあずかつた塩素が2.0モルになつた所で終
了することが収率および純度の点で好ましい。こ
のようにして得られたビス（２−クロロ−４−ト
リフルオロメチルフエニル）カーボネートは、収
率95％以上、純度95％以上で得られ工業的に容易
かつ安価に製造できる。 The reaction temperature is 30-150°C, preferably 70-110°C. The rate of chlorine gas introduction is adjusted within a range that can suppress the escape of chlorine gas so as to maintain this temperature. From the viewpoints of yield and purity, it is preferable that the amount of introduced chlorine is stopped when 2.0 moles of chlorine are involved in the reaction per mole of bis(4-trifluoromethylphenyl) carbonate. The bis(2-chloro-4-trifluoromethylphenyl) carbonate thus obtained has a yield of 95% or more and a purity of 95% or more, and can be produced industrially easily and inexpensively.
以下本発明を実施例により詳細に説明する。 The present invention will be explained in detail below using examples.
実施例 １
温度計、コンデンサー、かきまぜ機および塩素
導入管を付した２の四ツ口フラスコに350部の
ビス（４−トリフルオロメチルフエニル）カーボ
ネートと875部の１，１，２，２−テトラクロロ
エタンを仕込み、かきまぜ下に溶解させる。この
中に3.5部の無水塩化第２鉄（FeCl3）を添加し、
95〜100℃を保つて塩素ガスを29.8部／時間の速
度で５時間導入した。発生塩酸中の未反応塩素分
は4.7モル％であつた。導入終了後、窒素抜気を
１時間行なつた。反応液を室温まで冷却し、５％
塩酸水および水で洗浄後、脱水した後１，１，
２，２−テトラクロロエタンを留去し、418.1部
のビス（２−クロロ−４−トリフルオロメチルフ
エニル）カーボネートを得た。ガスクロマトグラ
フイーにより分析した結果、純度99.5％、収率
99.3％を得た。元素分析値は次に示す結果を得
た。Example 1 350 parts of bis(4-trifluoromethylphenyl) carbonate and 875 parts of 1,1,2,2- Charge tetrachloroethane and dissolve while stirring. Add 3.5 parts of anhydrous ferric chloride (FeCl 3 ) to this,
While maintaining the temperature at 95-100°C, chlorine gas was introduced at a rate of 29.8 parts/hour for 5 hours. The unreacted chlorine content in the generated hydrochloric acid was 4.7 mol%. After the introduction, nitrogen was vented for 1 hour. Cool the reaction solution to room temperature and add 5%
After washing with hydrochloric acid and water and dehydrating, 1,1,
2,2-tetrachloroethane was distilled off to obtain 418.1 parts of bis(2-chloro-4-trifluoromethylphenyl) carbonate. As a result of analysis by gas chromatography, purity is 99.5%, yield
Obtained 99.3%. The following elemental analysis results were obtained.
Ｃ Ｈ Cl Ｆ
理論値 42.96％ 1.43％ 16.95％ 27.21％
実測値 42.95 1.44 17.00 27.20
実施例 ２
塩素化触媒をSbCl5Eに代えた他は実施例１と
同様に反応して、418.6部のビス（２−クロロ−
４−トリフルオロメチルフエニル）カーボネート
を得た。ガスクロマトグラフイーにより分析した
結果、純度99.1％、収率99.0％を得た。 C H Cl F Theoretical value 42.96% 1.43% 16.95% 27.21% Actual value 42.95 1.44 17.00 27.20 Example 2 The reaction was carried out in the same manner as in Example 1 except that SbCl 5 E was used as the chlorination catalyst, and 418.6 parts of bis( 2-chloro-
4-trifluoromethylphenyl) carbonate was obtained. Analysis by gas chromatography showed a purity of 99.1% and a yield of 99.0%.
実施例 ３
実施例１と同じ装置を用い、350部のビス（４
−トリフルオロメチルフエニル）カーボネートと
1120部の四塩化炭素とを仕込みかきまぜ下に溶解
させる。この中に3.5部の無水塩化第２鉄
（FeCl3）を添加し、70〜75℃を保つて塩素ガス
を7.45部／時間の速度で20時間導入した。発生塩
酸中の未反応塩素分は4.5モル％であつた。以下
実施例１と同様に処理し、417.7部のビス（２−
クロロ−４−トリフルオロメチルフエニル）カー
ボネートを得た。Example 3 Using the same equipment as in Example 1, 350 parts of screws (4
-trifluoromethylphenyl)carbonate and
Add 1120 parts of carbon tetrachloride and dissolve while stirring. To this was added 3.5 parts of anhydrous ferric chloride (FeCl 3 ), and while maintaining the temperature at 70 to 75° C., chlorine gas was introduced at a rate of 7.45 parts/hour for 20 hours. The unreacted chlorine content in the generated hydrochloric acid was 4.5 mol%. The following treatment was carried out in the same manner as in Example 1, and 417.7 parts of screws (2-
Chloro-4-trifluoromethylphenyl) carbonate was obtained.
ガスクロマトグラフイーにより分析した結果、
純度98.8％、収率は98.5％であつた。 As a result of analysis by gas chromatography,
The purity was 98.8% and the yield was 98.5%.
Claims (1)
ーボネートを不活性有機溶剤に溶解し、ルイス酸
触媒存在下に塩素ガスと反応させ、選択的にビス
（２−クロロ−４−トリフルオロメチルフエニル）
カーボネートを得ることを特徴とするビス（２−
クロロ−４−トリフルオロメチルフエニル）カー
ボネートの製造法。1 Dissolve bis(4-trifluoromethylphenyl) carbonate in an inert organic solvent and react with chlorine gas in the presence of a Lewis acid catalyst to selectively form bis(2-chloro-4-trifluoromethylphenyl).
Bis(2-
Method for producing chloro-4-trifluoromethylphenyl) carbonate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57109965A JPS591444A (en) | 1982-06-28 | 1982-06-28 | Preparation of bis(2-chloro-4-trifluoromethylphenyl) carbonate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57109965A JPS591444A (en) | 1982-06-28 | 1982-06-28 | Preparation of bis(2-chloro-4-trifluoromethylphenyl) carbonate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS591444A JPS591444A (en) | 1984-01-06 |
| JPH0235744B2 true JPH0235744B2 (en) | 1990-08-13 |
Family
ID=14523636
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57109965A Granted JPS591444A (en) | 1982-06-28 | 1982-06-28 | Preparation of bis(2-chloro-4-trifluoromethylphenyl) carbonate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS591444A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012144306A1 (en) * | 2011-04-22 | 2012-10-26 | 宇部興産株式会社 | Nonaqueous electrolyte solution, electricity storage device using same, and trifluoromethylbenzene compound |
-
1982
- 1982-06-28 JP JP57109965A patent/JPS591444A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS591444A (en) | 1984-01-06 |
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