JPH0216746B2 - - Google Patents
Info
- Publication number
- JPH0216746B2 JPH0216746B2 JP11348083A JP11348083A JPH0216746B2 JP H0216746 B2 JPH0216746 B2 JP H0216746B2 JP 11348083 A JP11348083 A JP 11348083A JP 11348083 A JP11348083 A JP 11348083A JP H0216746 B2 JPH0216746 B2 JP H0216746B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- reaction
- potassium fluoride
- chlorobenzonitrile
- solvent
- 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
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 16
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- -1 chlorobenzonitrile compound Chemical class 0.000 claims description 8
- 235000003270 potassium fluoride Nutrition 0.000 claims description 8
- 239000011698 potassium fluoride Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- GDHXJNRAJRCGMX-UHFFFAOYSA-N 2-fluorobenzonitrile Chemical class FC1=CC=CC=C1C#N GDHXJNRAJRCGMX-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 description 2
- BNBRIFIJRKJGEI-UHFFFAOYSA-N 2,6-difluorobenzonitrile Chemical compound FC1=CC=CC(F)=C1C#N BNBRIFIJRKJGEI-UHFFFAOYSA-N 0.000 description 2
- NHWQMJMIYICNBP-UHFFFAOYSA-N 2-chlorobenzonitrile Chemical group ClC1=CC=CC=C1C#N NHWQMJMIYICNBP-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- INICGXSKJYKEIV-UHFFFAOYSA-N 2,3,4,5,6-pentachlorobenzonitrile Chemical compound ClC1=C(Cl)C(Cl)=C(C#N)C(Cl)=C1Cl INICGXSKJYKEIV-UHFFFAOYSA-N 0.000 description 1
- QTUXEYXZJLVGOA-UHFFFAOYSA-N 2,3,6-trichlorobenzonitrile Chemical compound ClC1=CC=C(Cl)C(C#N)=C1Cl QTUXEYXZJLVGOA-UHFFFAOYSA-N 0.000 description 1
- PGODHCIOIPODFE-UHFFFAOYSA-N 2,4,6-trichlorobenzonitrile Chemical compound ClC1=CC(Cl)=C(C#N)C(Cl)=C1 PGODHCIOIPODFE-UHFFFAOYSA-N 0.000 description 1
- HTKFGTCCOJIUIK-UHFFFAOYSA-N 2,4,6-trifluorobenzonitrile Chemical compound FC1=CC(F)=C(C#N)C(F)=C1 HTKFGTCCOJIUIK-UHFFFAOYSA-N 0.000 description 1
- GRUHREVRSOOQJG-UHFFFAOYSA-N 2,4-dichlorobenzonitrile Chemical compound ClC1=CC=C(C#N)C(Cl)=C1 GRUHREVRSOOQJG-UHFFFAOYSA-N 0.000 description 1
- LJFDXXUKKMEQKE-UHFFFAOYSA-N 2,4-difluorobenzonitrile Chemical compound FC1=CC=C(C#N)C(F)=C1 LJFDXXUKKMEQKE-UHFFFAOYSA-N 0.000 description 1
- CARZIMSIYVZQDB-UHFFFAOYSA-N 3,5-dichloro-2,4,6-trifluorobenzonitrile Chemical compound FC1=C(Cl)C(F)=C(C#N)C(F)=C1Cl CARZIMSIYVZQDB-UHFFFAOYSA-N 0.000 description 1
- UPMXOELFJREBOG-UHFFFAOYSA-N 3,5-dichloro-2,6-difluorobenzonitrile Chemical compound FC1=C(Cl)C=C(Cl)C(F)=C1C#N UPMXOELFJREBOG-UHFFFAOYSA-N 0.000 description 1
- QYALCKFGISNFMJ-UHFFFAOYSA-N 3-chloro-2,6-difluorobenzonitrile Chemical compound FC1=CC=C(Cl)C(F)=C1C#N QYALCKFGISNFMJ-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明は、クロロベンゾニトリル系化合物とフ
ツ化カリウムとを無溶媒、加圧下で反応させて、
各種農薬、医薬或いは染料などの中間原料として
有用なフルオロベンゾニトリル系化合物を製造す
る方法に関する。
従来、２，４又は６位に少なくとも１ケの塩素
原子を有するクロロベンゾニトリル系化合物（以
下CBN系化合物と略す）の２，４又は６位の総
ての塩素原子をフツ素原子に置換したフルオロベ
ンゾニトリル系化合物（以下FBN系化合物と略
す）を製造する方法としては、例えばJ.Chem.
Soc.、Chem.Comm.、1965、430〜431頁及有機
合成化学協会誌、第27巻、175頁（1969）に記載
された方法が知られている。これらの方法は、ジ
メチルスルホン或いはジメチルスルホキシドなど
の溶媒の存在下を条件とする製法に関するもので
あつて、そのため溶媒の分解により分離し難い生
成物が多量に存在するので後処理上難点があり、
更には溶媒を多量に用いる必要があるが利用した
溶媒の回収は、実質的には不可能な状態であるの
で、経済的に不利であり、これら従来の方法に代
わるより工業的有利な方法の出現が求められてい
る。
本発明者達は、前述の方法を改良すべく検討を
重ねた結果、加圧下で反応させることによつて、
無溶媒でも高収率で目的物が得られることの知見
を得、新規でかつ工業的有利な製造方法として本
発明完成するに至つた。
すなわち本発明は、２，４又は６位に少なくと
も１ケの塩素原子を有するクロロベンゾニトリル
系化合物とフツ化カリウムとを反応させて、２，
４又は６位の総ての塩素原子をフツ素原子に置換
したフルオロベンゾニトリル系化合物を製造する
方法において、前記クロロベンゾニトリル系化合
物とフツ化カリウムとを無溶媒で、加圧下、200
〜450℃で反応させることを特徴とするフルオロ
ベンゾニトリル系化合の製造方法である。
本発明で用い原料物質のCBN系化合物は、次
の一般式（）
（X1及びX2は各々水素原子又は塩素原子であり、
ｌ、ｍ及びｎは０又は１であり、ｌ、ｍ又はｎの
少なくとも１ケは１である。）で表わされ、従つ
て本発明で得られるFBN系化合物は、次の一般
式（）
（X1、Ｘ、ｌ、ｍ及びｎは前述の通りである。）
で表わされる。例えば、CBN系化合物として２
−クロロベンゾニトリル、２，４−ジクロロベン
ゾニトリル、２，６−ジクロロベンゾニトリル、
２，４，６−トリクロロベンゾニトリル、２，
３，６−トリクロロベンゾニトリル、２，３，
５，６−テトラクロロベンゾニトリル、或いは
２，３，４，５，６−ペンタクロロベンゾニトリ
ルなどを用い、所定のフツ素置換反応を実施する
と、FBN系化合物としては、２−フルオロベゾ
ニトリル（B.P.103℃／35mmHg）２，４−ジフル
オロベンゾニトリル（M.P.46〜47℃）、２，６−
ジフルオロベンゾニトリル（B.P.81〜83℃／13mm
Hg）２，４，６−トリフルオロベンゾニトリル
（B.P.106〜108℃／75mmHg）、３−クロロ−２，
６−ジフルオロベンゾニトリル（B.P.95℃／11mm
Hg）、３，５−ジクロロ−２，６−ジフルオロベ
ンゾニトリル（B.P.100℃／10mmHg）或いは３，
５−ジクロロ−２，４，６−トリフルオベンゾニ
トリル（B.P.221℃）などが好適に得られる。
本発明方法の実施に当つては、オートクレーブ
などの密閉容器中にCBN系化合物とフツ化カリ
ウムとを投入し、加熱、撹拌することによつて行
なわれる。
ここで用いられるフツ化カリウムは、通常の市
販品或いは極微粒物などいずれのものでも用いる
ことができ、その使用量は、CBN系化合物の２，
４又は６位の総ての塩素原子をフツ素原子に置換
する反応理論量の0.8〜2.0倍、望ましくは１〜1.5
倍である。一般には反応温度は200〜450℃、望ま
しくは300〜400℃であり、反応時間は、0.5〜30
時間である。密閉容器中の圧力は、密閉加熱によ
る自然加圧でよく、その場合圧力は大凡３Kg／cm2
〜25Kg／cm2程度である。尚、不活性気体により密
閉容器中の空気を置換したり或いは、前記圧力範
囲以上に加圧しても良く、この場合酸化或いは重
合等を防止することもできる。
この様にして得られた反応生成物は、通常の分
離、精製手段を施すことによつて、或いは施さず
して目的物であるFBN系化合物を高純度、高収
率で得ることができる。尚、未反応原料や未反応
生成物が反応生成物中に存在する場合には、例え
ば蒸留などの分離手段を施して未反応物を回収
し、循環使用することができる。
次に本発明の実施例を記載する。
実施例 １
圧力計、撹拌機及び温度計を備えた500mlのオ
ートクレーブに、２，６−ジクロロベンゾニトリ
ル111.8ｇ（純度96％）及びフツ化カリウム108.8
ｇを投入し、オートクレーブを密閉した。次に乾
燥窒素ガスでオートクレーブ中の空気を置換し、
撹拌下徐々に昇温して内温が350℃になつた時点
から３時間反応させた。尚、この間の最大圧力は
14.3Kg／cm2であつた。反応終了後、冷却降温し、
200℃近辺より予めオートクレーブに付設した蒸
留回収装置を用いた生成物を採集し、73.0ｇの油
状物を得た。
この油状物質をガスクロマトグラフイーで分析
した結果、２，６−ジフルオロベンゾニトリルの
含有率は99％であつた。（収率83％）
実施例 ２〜６
前記実施例１の場合と同様にして反応させ、次
表の結果を得た。
【表】Detailed Description of the Invention The present invention involves reacting a chlorobenzonitrile compound and potassium fluoride without a solvent under pressure.
The present invention relates to a method for producing fluorobenzonitrile compounds useful as intermediate raw materials for various agricultural chemicals, medicines, dyes, etc. Conventionally, all chlorine atoms at the 2, 4, or 6 positions of chlorobenzonitrile compounds (hereinafter referred to as CBN compounds) having at least one chlorine atom at the 2, 4, or 6 positions were replaced with fluorine atoms. As a method for producing fluorobenzonitrile compounds (hereinafter referred to as FBN compounds), for example, J.Chem.
The methods described in Soc., Chem.Comm., 1965, pp. 430-431 and Journal of the Society of Organic Synthetic Chemistry, Vol. 27, p. 175 (1969) are known. These methods involve production methods that require the presence of a solvent such as dimethyl sulfone or dimethyl sulfoxide, and as a result, there are many products that are difficult to separate due to decomposition of the solvent, which poses difficulties in post-processing.
Furthermore, although it is necessary to use a large amount of solvent, it is virtually impossible to recover the used solvent, which is economically disadvantageous. Appearance is required. As a result of repeated studies to improve the above-mentioned method, the inventors of the present invention discovered that by reacting under pressure,
It was found that the desired product can be obtained in high yield even without a solvent, and the present invention was completed as a new and industrially advantageous production method. That is, the present invention involves reacting a chlorobenzonitrile compound having at least one chlorine atom at the 2, 4 or 6 position with potassium fluoride,
In a method for producing a fluorobenzonitrile compound in which all chlorine atoms at the 4 or 6 positions are substituted with fluorine atoms, the chlorobenzonitrile compound and potassium fluoride are mixed in a solvent-free manner under pressure at 200 g.
This is a method for producing a fluorobenzonitrile compound, characterized by carrying out the reaction at ~450°C. The CBN compound as a raw material used in the present invention has the following general formula () (X 1 and X 2 are each a hydrogen atom or a chlorine atom,
l, m and n are 0 or 1, and at least one of l, m or n is 1. ), therefore, the FBN-based compound obtained in the present invention has the following general formula () (X 1 , X, l, m and n are as described above.)
It is expressed as For example, as a CBN compound, 2
-chlorobenzonitrile, 2,4-dichlorobenzonitrile, 2,6-dichlorobenzonitrile,
2,4,6-trichlorobenzonitrile, 2,
3,6-trichlorobenzonitrile, 2,3,
When a predetermined fluorine substitution reaction is performed using 5,6-tetrachlorobenzonitrile or 2,3,4,5,6-pentachlorobenzonitrile, etc., the FBN-based compound is 2-fluorobezonitrile. (BP103℃/35mmHg) 2,4-difluorobenzonitrile (MP46-47℃), 2,6-
Difluorobenzonitrile (BP81~83℃/13mm
Hg) 2,4,6-trifluorobenzonitrile (BP106-108℃/75mmHg), 3-chloro-2,
6-difluorobenzonitrile (BP95℃/11mm
Hg), 3,5-dichloro-2,6-difluorobenzonitrile (BP100℃/10mmHg) or 3,
5-dichloro-2,4,6-trifluorobenzonitrile (BP221°C) and the like are preferably obtained. In carrying out the method of the present invention, a CBN compound and potassium fluoride are placed in a closed container such as an autoclave, and the mixture is heated and stirred. The potassium fluoride used here can be either a commercially available product or an ultrafine powder, and the amount used is the same as that of the CBN-based compound.
0.8 to 2.0 times, preferably 1 to 1.5 times the theoretical amount of the reaction to replace all 4 or 6 chlorine atoms with fluorine atoms.
It's double. Generally, the reaction temperature is 200-450℃, preferably 300-400℃, and the reaction time is 0.5-30℃.
It's time. The pressure in the sealed container may be natural pressure due to sealed heating, in which case the pressure is approximately 3Kg/cm 2
~25Kg/ cm2 . Note that the air in the closed container may be replaced with an inert gas, or the pressure may be increased above the above pressure range, and in this case, oxidation, polymerization, etc. can be prevented. The reaction product thus obtained can be subjected to conventional separation and purification means, or the target FBN compound can be obtained with high purity and high yield. Incidentally, if unreacted raw materials or unreacted products are present in the reaction product, the unreacted materials can be recovered by performing a separation means such as distillation, and recycled for use. Next, examples of the present invention will be described. Example 1 In a 500 ml autoclave equipped with a pressure gauge, stirrer and thermometer, 111.8 g of 2,6-dichlorobenzonitrile (96% purity) and 108.8 g of potassium fluoride were added.
g and the autoclave was sealed. Next, replace the air in the autoclave with dry nitrogen gas,
The temperature was gradually raised while stirring, and the reaction was continued for 3 hours from the time when the internal temperature reached 350°C. The maximum pressure during this period is
It was 14.3Kg/ cm2 . After the reaction is completed, the temperature is lowered and
The product was collected from around 200°C using a distillation recovery device attached to the autoclave in advance, and 73.0 g of oil was obtained. Analysis of this oily substance by gas chromatography revealed that the content of 2,6-difluorobenzonitrile was 99%. (Yield: 83%) Examples 2 to 6 The reaction was carried out in the same manner as in Example 1, and the results shown in the following table were obtained. 【table】
Claims (1)
を有するクロロベンゾニトリル系化合物とフツ化
カリウムとを反応させて、２，４又は６位の総て
の塩素原子をフツ素原子に置換したフルオロベン
ゾニトリル系化合物を製造する方法において、前
記クロロベンゾニトリル系化合物とフツ化カリウ
ムとを無溶媒で、加圧下、200〜450℃で反応させ
ることを特徴とするフルオロベンゾニトリル系化
合物の製造方法。1 A chlorobenzonitrile compound having at least one chlorine atom at the 2, 4 or 6 position was reacted with potassium fluoride to replace all chlorine atoms at the 2, 4 or 6 position with fluorine atoms. A method for producing a fluorobenzonitrile compound, the method comprising reacting the chlorobenzonitrile compound and potassium fluoride without a solvent at 200 to 450°C under pressure. .
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11348083A JPS604159A (en) | 1983-06-23 | 1983-06-23 | Production of fluorobenzonitrile compound |
| GB08415348A GB2142018B (en) | 1983-06-23 | 1984-06-15 | Method for producing 2,6-difluorobenzonitrile |
| DE19843422936 DE3422936A1 (en) | 1983-06-23 | 1984-06-20 | METHOD FOR PRODUCING 2,6-DIFLUORBENZONITRILE |
| FR8409817A FR2549048B1 (en) | 1983-06-23 | 1984-06-22 | PROCESS FOR THE PREPARATION OF 2,6-DIFLUOROBENZONITRILE FROM 2,6-DICHLOROBENZONITRILE |
| CH303784A CH660361A5 (en) | 1983-06-23 | 1984-06-22 | METHOD FOR PRODUCING 2,6-DIFLUORBENZONITRILE. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11348083A JPS604159A (en) | 1983-06-23 | 1983-06-23 | Production of fluorobenzonitrile compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS604159A JPS604159A (en) | 1985-01-10 |
| JPH0216746B2 true JPH0216746B2 (en) | 1990-04-18 |
Family
ID=14613344
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11348083A Granted JPS604159A (en) | 1983-06-23 | 1983-06-23 | Production of fluorobenzonitrile compound |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS604159A (en) |
| CH (1) | CH660361A5 (en) |
| DE (1) | DE3422936A1 (en) |
| FR (1) | FR2549048B1 (en) |
| GB (1) | GB2142018B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6023358A (en) * | 1983-07-19 | 1985-02-05 | Ishihara Sangyo Kaisha Ltd | 2,4,6-trifluorobenzonitrile |
| US5200548A (en) * | 1984-06-04 | 1993-04-06 | Bayer Aktiengesellschaft | 2,4,5-Trihalogeno- and 2,3,4,5-tetrahalogenobenzene derivatives |
| US5530158A (en) * | 1984-06-04 | 1996-06-25 | Bayer Aktiengesellschaft | 2,4,5-trihalogeno- and 2,3,4,5-tetrahalogenobenzene derivatives |
| US5502235A (en) * | 1994-12-28 | 1996-03-26 | Dowelanco | Solventless process for making 2,6 difluorobenzonitrile |
| US6437168B1 (en) | 2000-09-05 | 2002-08-20 | Nippon Shokubai Co., Ltd. | Method for production of aromatic fluorine compound |
| CN104387289B (en) * | 2014-10-30 | 2017-09-01 | 天津河清化学工业有限公司 | The method of catalyst amount is reduced in difluorobenzonilyile production |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1026290A (en) * | 1964-03-17 | 1966-04-14 | Robert Neville Haszeldine | Aromatic fluorine compounds |
| US3240824A (en) * | 1965-01-28 | 1966-03-15 | Olin Mathieson | Process for preparing fluoronitrobenzenes |
-
1983
- 1983-06-23 JP JP11348083A patent/JPS604159A/en active Granted
-
1984
- 1984-06-15 GB GB08415348A patent/GB2142018B/en not_active Expired
- 1984-06-20 DE DE19843422936 patent/DE3422936A1/en active Granted
- 1984-06-22 CH CH303784A patent/CH660361A5/en not_active IP Right Cessation
- 1984-06-22 FR FR8409817A patent/FR2549048B1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS604159A (en) | 1985-01-10 |
| GB2142018B (en) | 1986-12-10 |
| GB2142018A (en) | 1985-01-09 |
| DE3422936C2 (en) | 1989-11-16 |
| FR2549048B1 (en) | 1987-12-24 |
| CH660361A5 (en) | 1987-04-15 |
| DE3422936A1 (en) | 1985-01-03 |
| GB8415348D0 (en) | 1984-07-18 |
| FR2549048A1 (en) | 1985-01-18 |
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