JPS6345231A - Production of 3,4-dichloro-6-trifluoromethyltoluene - Google Patents
Production of 3,4-dichloro-6-trifluoromethyltolueneInfo
- Publication number
- JPS6345231A JPS6345231A JP61188575A JP18857586A JPS6345231A JP S6345231 A JPS6345231 A JP S6345231A JP 61188575 A JP61188575 A JP 61188575A JP 18857586 A JP18857586 A JP 18857586A JP S6345231 A JPS6345231 A JP S6345231A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- dichloro
- ccl4
- reaction product
- compound
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- OARYHYOOIUIKFZ-UHFFFAOYSA-N 1,2-dichloro-4-methyl-5-(trifluoromethyl)benzene Chemical compound CC1=CC(Cl)=C(Cl)C=C1C(F)(F)F OARYHYOOIUIKFZ-UHFFFAOYSA-N 0.000 title claims 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims abstract description 24
- WYUIWKFIFOJVKW-UHFFFAOYSA-N 1,2-dichloro-4-methylbenzene Chemical compound CC1=CC=C(Cl)C(Cl)=C1 WYUIWKFIFOJVKW-UHFFFAOYSA-N 0.000 claims abstract description 10
- -1 aluminum halide Chemical class 0.000 claims description 11
- 229910052782 aluminium Inorganic materials 0.000 claims description 8
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 5
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 5
- CBXDCGQZMAUIHD-UHFFFAOYSA-N 1-methyl-2-(trichloromethyl)benzene Chemical compound CC1=CC=CC=C1C(Cl)(Cl)Cl CBXDCGQZMAUIHD-UHFFFAOYSA-N 0.000 claims 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract description 10
- 239000007795 chemical reaction product Substances 0.000 abstract description 7
- 239000007864 aqueous solution Substances 0.000 abstract description 3
- 238000009835 boiling Methods 0.000 abstract description 3
- JZWZPWDFZGTMIF-UHFFFAOYSA-N 1,2-dichloro-4-methyl-5-(trichloromethyl)benzene Chemical compound CC1=CC(Cl)=C(Cl)C=C1C(Cl)(Cl)Cl JZWZPWDFZGTMIF-UHFFFAOYSA-N 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 4
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 239000003905 agrochemical Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 238000005292 vacuum distillation Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 238000003682 fluorination reaction Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- DLESTTCLFWLCBX-UHFFFAOYSA-N 1,2-dichloro-5-methyl-3-(trifluoromethyl)benzene Chemical compound CC1=CC(Cl)=C(Cl)C(C(F)(F)F)=C1 DLESTTCLFWLCBX-UHFFFAOYSA-N 0.000 description 1
- DVFVNJHIVAPTMS-UHFFFAOYSA-N 1-methyl-2-(trifluoromethyl)benzene Chemical compound CC1=CC=CC=C1C(F)(F)F DVFVNJHIVAPTMS-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 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
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、医・ａ薬の原料として極めて有用な３．４−
ジクロロ−６−トリフルオロメチルトルエン（以下０Ｃ
ＴＰＴと略す。）の製造法に関するものである。Detailed Description of the Invention [Field of Industrial Application] The present invention provides 3.4-
Dichloro-6-trifluoromethyltoluene (hereinafter referred to as 0C
It is abbreviated as TPT. ).
ＤＣＴＰＴの製造法としては、以下のものが知られてい
る。The following methods are known as methods for producing DCTPT.
Ａ＋Ｍａｒｈｏｌｄ ａｎｄ Ｅ、に１ａｕｋｅ、 ｊ
ｏｕｒｎａｌ ｏｆ ＦｌｕｏｒｉｎｅＣｈｅｓ＋１ｓ
ｔｒｙ、 ２８１〜２９１ （１９８１）２０：３
しかしながら、３．４−ジクロロ−トルエン（以下でＯ
ＣＴと略す）の反応率が２５％と低（、またＤＣＴＰＴ
の異性体である３、４−ジクロロ−５−トリフルオロメ
チルトルエンが副生するため分離・ネδ製が困難であり
、さらには反応中にフロン１１が副生ずるため弗化水素
、四塩化炭素の反応選択率も低い、等の問題点を有して
いた。A+Marhold and E, ni1auke, j
Oural of FluorineChes+1s
try, 281-291 (1981) 20:3 However, 3,4-dichloro-toluene (hereinafter O
The reaction rate of CT (abbreviated as CT) is as low as 25% (also DCTPT).
Since 3,4-dichloro-5-trifluoromethyltoluene, which is an isomer of It had problems such as low reaction selectivity.
本発明者らは、収串良＜ ０ＣＴＰＴを得るべく説、！
検討の結果、本発明に到達した。The inventors of the present invention aim to obtain a yield of <0CTPT!
As a result of study, we have arrived at the present invention.
すなわち、本発明はハロゲン化アルミニウムの存在下に
、３．４−ジクロロトルエンと四塩化炭素とを反応させ
、３．４−ジクロロ−６−トリクロロメチルトルエン（
以下ＤＣＴＣＴと略す）を回収し、これをフッ化水素と
反応せしめることを特徴とする３、４〜ジクロロ−６−
トリフルオロメチルトルエンの製造法である。That is, in the present invention, 3,4-dichlorotoluene and carbon tetrachloride are reacted in the presence of aluminum halide to produce 3,4-dichloro-6-trichloromethyltoluene (
3,4-dichloro-6-
This is a method for producing trifluoromethyltoluene.
本発明において、中間生成物として回収するＤＣＴＣＴ
は下記の反応式に示す通り、ＯＣＴと四塩化炭素とをハ
ロゲン化アルミニウムの存在下に反応させることにより
３．４−ジクロロ−５−トリクロロメチルトルエンを生
成すること＃なしに、容易且つ高収率で製造できる。In the present invention, DCTCT recovered as an intermediate product
As shown in the reaction formula below, 3,4-dichloro-5-trichloromethyltoluene can be produced easily and in high yield by reacting OCT and carbon tetrachloride in the presence of aluminum halide. It can be manufactured at a high rate.
本反応に於ける四塩化炭素の使用量はＤＣＴに対して、
１〜２０倍モル使用し、反応溶媒として用いても良い。The amount of carbon tetrachloride used in this reaction is
It may be used in an amount of 1 to 20 times the mole and used as a reaction solvent.
本反応に於けるハロゲン化アルミニウムとしては、無水
塩化アルミニウム、無水臭化アルミニウムなどが挙げら
れる。ハロゲン化アルミニウムの使用量はＯＣＴに対し
て０．５〜５倍モル、望ましくは１〜３倍モルである。Examples of the aluminum halide in this reaction include anhydrous aluminum chloride and anhydrous aluminum bromide. The amount of aluminum halide used is 0.5 to 5 times the mole of OCT, preferably 1 to 3 times the mole.
ハロゲン化アルミニウムはＤＣＴＣＴと下式に示すよう
な錯体【】］
を形成するため、ハロゲン化アルミニウム力不足する場
合には、下式に示すジクロロビス（３゜４−シクロロー
６−メチルフェニル）メタン（ＩＦＦＤＣＢＭと略す）
なる副生成物が選択的に生成する。なお、３．４−ジク
ロロ−ビス（トリクロロメチル）トルエン（以下ＤＣＢ
Ｔと略す）の生成は認められなかった。Aluminum halide forms a complex []] with DCTCT as shown in the formula below, so if aluminum halide is insufficient, dichlorobis(3°4-cyclo-6-methylphenyl)methane (IFFDCBM) as shown in the formula below can be used. (abbreviated as ) is selectively produced. In addition, 3,4-dichloro-bis(trichloromethyl)toluene (hereinafter referred to as DCB
(abbreviated as T) was not observed.
又、ハロゲン化アルミニウムの使用量は、ＤＣＴに対し
て２倍モルが最も望ましい。The most desirable amount of aluminum halide to be used is twice the molar amount of DCT.
本反応の反応温度は０〜１００℃であり、望ましくは２
０〜８０℃である０反応温度が高い場合にはＤＣＢＭの
選択率が増加し、低い場合には反応速度が著しく低下す
るため、更に望ましくは４０〜６０℃である。The reaction temperature of this reaction is 0 to 100°C, preferably 2
If the reaction temperature is high (0 to 80°C), the selectivity of DCBM will increase, and if it is low, the reaction rate will be significantly reduced, so it is more preferably 40 to 60°C.
溶媒としては、例えば塩化メチレン、テトラクロロエタ
ン、フロン顛などが使用できるが、１．２−ジクロロエ
タンはＤＣＴＣＴの選択率を著しく向上させることの出
来る溶媒である。また、本反応の反応時間は一機に規定
できないが、２０分〜４時間である。このようにして得
た反応生成物に水を添加して錯体を分解し、目的のＤＣ
ＴＣＴを得る。As the solvent, for example, methylene chloride, tetrachloroethane, chlorofluorocarbon, etc. can be used, and 1,2-dichloroethane is a solvent that can significantly improve the selectivity of DCTCT. Further, although the reaction time of this reaction cannot be specified for one reaction, it is 20 minutes to 4 hours. Water is added to the reaction product thus obtained to decompose the complex, and the desired DC
Obtain TCT.
Ｄ ＣＴ ＣＴの弗素化反応は、耐蝕性のあるオートク
レーブ（例えば、５ｔｉＳ−３１６などを用いる）中に
、ｒ）ＣＴＣτと理論量以上の弗化水素を入れ、０〜１
５０℃望ましくは室温〜１００℃で行われる。D CT The fluorination reaction of CT is carried out by placing r) CTCτ and more than a theoretical amount of hydrogen fluoride in a corrosion-resistant autoclave (for example, using 5tiS-316), and
It is carried out at 50°C, preferably room temperature to 100°C.
又、反応圧は３〜２０ｋｇ／−望ましくは、８〜１０ｋ
ｇ／−で行われる。弗化水素量としては、ＤＣＴＣＴに
対して３．２〜１２倍モル望ましくは６〜９倍モルであ
る。In addition, the reaction pressure is 3 to 20 kg/-, preferably 8 to 10 kg/-
g/-. The amount of hydrogen fluoride is 3.2 to 12 times mole, preferably 6 to 9 times mole, relative to DCTCT.
反応生成物は、アルカリ水溶液により洗浄後、減圧蒸留
を行い反応溶媒および未反応の四塩化炭素、更には高沸
点反応生成物を除くことにより、純度の高い０ＣＴＦＴ
を容易に得ることが出来る。次に、本発明方法を実施例
により具体的に説明する。After washing the reaction product with an alkaline aqueous solution, it is distilled under reduced pressure to remove the reaction solvent, unreacted carbon tetrachloride, and high-boiling reaction products, resulting in highly pure 0CTFT.
can be easily obtained. Next, the method of the present invention will be specifically explained using examples.
実施例１
無水塩化アルミニウム２７．０ｇ （０，２０３モル）
と四塩化炭素１００．０ｇの混合液中に、攪拌下ＤＣ７
１６，１ｇ（０，１モル）と四塩化炭素５４ｇ（合計１
．０モル）の溶液を５０〜５２℃、２時間で滴加しさら
に２時間攪拌反応させた。放冷後、氷水７００ｍｊ！に
反応液を注ぎ室温下攪拌し塩化アルミニウムを除いた。Example 1 Anhydrous aluminum chloride 27.0g (0,203 mol)
and 100.0 g of carbon tetrachloride under stirring at DC7.
16.1g (0.1 mol) and 54g carbon tetrachloride (total 1
．． A solution of 0 mol) was added dropwise at 50 to 52° C. over 2 hours, and the reaction was stirred for further 2 hours. After cooling, 700 mj of ice water! The reaction solution was poured into a solution and stirred at room temperature to remove aluminum chloride.
水層を四塩化炭素で抽出し、集めた有機層を５％苛性ソ
ーダ水溶液で洗浄し、無水塩化カルシウムで乾燥し、溶
媒を減圧留去して粗ＤＣＴＣＴ ２５．２ｇを（また。The aqueous layer was extracted with carbon tetrachloride, the collected organic layer was washed with 5% aqueous sodium hydroxide solution, dried over anhydrous calcium chloride, and the solvent was distilled off under reduced pressure to obtain 25.2 g of crude DCTCT (also.
これをガスクロマトグラフィーで分析したところＤＣＴ
ＣＴが７３．３ｗｔ％（収率６６．３％） ＤＣＢＭが
１６．２ｗｔ％（収＄ ２０．３％）、ＤＣＢＴは検出
されず、また未反応のＯＣＴも検出されなかった。この
粗ＤＣＴＣＴ ： ２５．２ｇと弗化水素１０．９ｇを
１００ｍ１！のオートクレーブに仕込み、反応温度６０
〜８０℃で加温しながら攪拌し、反応圧が８ｋｇ／ｃ４
となるように還流塔上部から一次圧調整弁を用いて反応
副生成物である塩化水素ガスを連続的に抜き出した。約
３時間後、反応圧の上昇が總められない時点で、弗素化
が終了したと判断し反応生成物をオートクレーブから取
り出し、１０％苛性ソーダ水溶液で洗浄し未反応の弗化
水素を除去した後、減圧１留することにより、純度９８
．２％のＤＣＴＰＴ １２．８２ｇ （０，０５＋Ｏモ
ル、収率５５．０％）を（ｌた（沸点９７〜１００℃／
２３ｍｍ ｌ１ｇ）。When this was analyzed by gas chromatography, DCT
CT was 73.3 wt% (yield 66.3%), DCBM was 16.2 wt% (yield $20.3%), DCBT was not detected, and unreacted OCT was also not detected. This crude DCTCT: 25.2g and hydrogen fluoride 10.9g in 100ml! into an autoclave, and the reaction temperature was 60℃.
Stir while heating at ~80℃, reaction pressure is 8kg/c4
Hydrogen chloride gas, a reaction by-product, was continuously extracted from the upper part of the reflux column using a primary pressure regulating valve so that After about 3 hours, when the reaction pressure did not continue to rise, it was judged that the fluorination was completed, and the reaction product was taken out from the autoclave and washed with a 10% aqueous solution of caustic soda to remove unreacted hydrogen fluoride. , purity 98 by one distillation under reduced pressure.
．． 12.82 g of 2% DCTPT (0.05+O mol, yield 55.0%) was added (boiling point 97-100°C/
23mm l1g).
実施例２
無水塩化アルミニウム２７．０ｇ （０，２０３モル）
と四塩化炭素３１．５ｇ （０，２０５モル）と、１
．２−ジクロロエタン５０．５ｇ Ｏ）混合液中に、攪
拌下、３゜４−ジクロロトルエン１６．１ｇ （０，１
モル）と１．２−ジクロロエタン１９．１ｇの混合溶液
を滴加する以外は実施例１と同様の操作を行い、純度９
８．５％の０ＣＴＰＴ １５．１８ｇ （０，０６５モ
ル、収率６５．３ン６）を得た。Example 2 Anhydrous aluminum chloride 27.0g (0,203 mol)
and 31.5 g (0,205 mol) of carbon tetrachloride, and 1
．． 50.5 g of 2-dichloroethane (0,1
The same operation as in Example 1 was carried out except that a mixed solution of 19.1 g of 1,2-dichloroethane (mol) and 1,2-dichloroethane was added dropwise, and the purity was 9.
15.18 g (0,065 mol, yield 65.3 n6) of 8.5% 0CTPT were obtained.
特許出願人 セントラル鞘子株式会社（、−一一一二
一Patent applicant: Central Sayako Co., Ltd. (-11121)
Claims (1)
ルエンと四塩化炭素とを反応させ、３，４−ジクロロ−
６−トリクロロメチルトルエンを回収し、これをフッ化
水素と反応せしめることを特徴とする３，４−ジクロロ
−６−トリフルオロメチルトルエンの製造法3,4-dichlorotoluene and carbon tetrachloride are reacted in the presence of aluminum halide, and 3,4-dichloro-
A method for producing 3,4-dichloro-6-trifluoromethyltoluene, which comprises recovering 6-trichloromethyltoluene and reacting it with hydrogen fluoride.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61188575A JPS6345231A (en) | 1986-08-13 | 1986-08-13 | Production of 3,4-dichloro-6-trifluoromethyltoluene |
| US07/084,019 US4876404A (en) | 1986-08-13 | 1987-08-11 | Preparation of dichlorotrifluoromethyltoluenes including novel isomers |
| GB8719063A GB2194235B (en) | 1986-08-13 | 1987-08-12 | Dichlorotrifluoromethyltoluenes and preparation thereof |
| FR878711502A FR2602764B1 (en) | 1986-08-13 | 1987-08-12 | DICHLOROTRIFLUOROMETHYLTOLUENES COMPOUNDS AND PROCESS FOR THE PREPARATION THEREOF |
| DE19873726890 DE3726890A1 (en) | 1986-08-13 | 1987-08-12 | METHOD FOR THE PRODUCTION OF DICHLORTRIFLUORMETHYLTOLUOLS AND NEW ISOMERS PRODUCED BY THE METHOD |
| IT8721651A IT1228929B (en) | 1986-08-13 | 1987-08-13 | PREPARATION OF DICHLOROTRIFLUOROMETILTOLUENI, INCLUDING ISOMERS |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61188575A JPS6345231A (en) | 1986-08-13 | 1986-08-13 | Production of 3,4-dichloro-6-trifluoromethyltoluene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6345231A true JPS6345231A (en) | 1988-02-26 |
| JPH0474340B2 JPH0474340B2 (en) | 1992-11-26 |
Family
ID=16226080
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61188575A Granted JPS6345231A (en) | 1986-08-13 | 1986-08-13 | Production of 3,4-dichloro-6-trifluoromethyltoluene |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6345231A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03161450A (en) * | 1989-11-17 | 1991-07-11 | Asahi Glass Co Ltd | Production of novel fluorobenzotrichloride compound and fluorobenzoic acids |
-
1986
- 1986-08-13 JP JP61188575A patent/JPS6345231A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03161450A (en) * | 1989-11-17 | 1991-07-11 | Asahi Glass Co Ltd | Production of novel fluorobenzotrichloride compound and fluorobenzoic acids |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0474340B2 (en) | 1992-11-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0919527A1 (en) | Gas phase fluorination of 1,1,3,3-tetrachloro-2-propene | |
| JPS6212212B2 (en) | ||
| EP0462514A1 (en) | Process for preparing 1-chloro-2,2,2-trifluoroethane | |
| JPS6345231A (en) | Production of 3,4-dichloro-6-trifluoromethyltoluene | |
| JP2935436B2 (en) | Method for producing fluorinated benzoic acid | |
| EP1528052B1 (en) | Process for the production of 4-amino-3,5-dichlorobenzotrifluoride with high purity commercial products being obtained in parallel | |
| US4968852A (en) | Trifluoromethylbenzoyl bromide and conversion of same to bromobenzotrifluoride | |
| US4876404A (en) | Preparation of dichlorotrifluoromethyltoluenes including novel isomers | |
| EP1094053B1 (en) | Method of preparing fluoroaromatic compounds | |
| CN111943794B (en) | Preparation method of (7Z) -7-ditridecene | |
| US4760209A (en) | Process for preparing 3,5-dichloro-α-methylstyrene | |
| JP2672012B2 (en) | Method for producing 1-chloro-3,4-difluorobenzene | |
| EP0038052A1 (en) | Method for the preparation of cis-alkenyl bromide and acetate | |
| JP3952514B2 (en) | Method for producing 7-methyl-2-naphthalenecarbonitrile | |
| JP4303685B2 (en) | Method for producing 2-cyclopenten-1-one | |
| JP4749638B2 (en) | Production of tetrafluorohalogenbenzene | |
| KR810001279B1 (en) | Preparation of meta-aryloxy-benzaldehydes | |
| US4392929A (en) | Preparation of bis-(1-bromo-2,3,3-trichloro-2-propenyl) ether | |
| JPH0713043B2 (en) | 3,4-Dichloro-6-trifluoromethyl-toluene derivative and process for producing the same | |
| JPH07165638A (en) | New fluorobenzotrichloride compound | |
| JPS63270632A (en) | Novel dichlorotrifluoromethyltoluene and production thereof | |
| JPH07206732A (en) | Production of 1-bromoalkylbenzene derivative | |
| JPH0147403B2 (en) | ||
| KR19990028862A (en) | Method for preparing alpha, omega-bromochloroalkane | |
| JPH05132446A (en) | Preparation of beta-halogeno-tert-alkylcarboxy- lic acid chlorides |