JPS6350339B2 - - Google Patents
Info
- Publication number
- JPS6350339B2 JPS6350339B2 JP59090200A JP9020084A JPS6350339B2 JP S6350339 B2 JPS6350339 B2 JP S6350339B2 JP 59090200 A JP59090200 A JP 59090200A JP 9020084 A JP9020084 A JP 9020084A JP S6350339 B2 JPS6350339 B2 JP S6350339B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- derivative
- fluoronitrobenzene
- chloronitrobenzene
- active halogen
- 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
- 150000001875 compounds Chemical class 0.000 claims description 12
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical class [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 claims description 11
- PWKNBLFSJAVFAB-UHFFFAOYSA-N 1-fluoro-2-nitrobenzene Chemical class [O-][N+](=O)C1=CC=CC=C1F PWKNBLFSJAVFAB-UHFFFAOYSA-N 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 229910001512 metal fluoride Inorganic materials 0.000 claims description 5
- 239000002798 polar solvent Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 19
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- FYXKZNLBZKRYSS-UHFFFAOYSA-N benzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C(Cl)=O FYXKZNLBZKRYSS-UHFFFAOYSA-N 0.000 description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
- 239000011698 potassium fluoride Substances 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 5
- 239000011521 glass Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000003682 fluorination reaction Methods 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- RBAHXNSORRGCQA-UHFFFAOYSA-N 1-chloro-2-fluoro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1F RBAHXNSORRGCQA-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- CMVQZRLQEOAYSW-UHFFFAOYSA-N 1,2-dichloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1Cl CMVQZRLQEOAYSW-UHFFFAOYSA-N 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- RZKKOBGFCAHLCZ-UHFFFAOYSA-N 1,4-dichloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1Cl RZKKOBGFCAHLCZ-UHFFFAOYSA-N 0.000 description 1
- LOTKRQAVGJMPNV-UHFFFAOYSA-N 1-fluoro-2,4-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C([N+]([O-])=O)=C1 LOTKRQAVGJMPNV-UHFFFAOYSA-N 0.000 description 1
- RXNOYRCWKRFNIM-UHFFFAOYSA-N 2-carbonochloridoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(Cl)=O RXNOYRCWKRFNIM-UHFFFAOYSA-N 0.000 description 1
- DIAWBHLTWNWYGR-UHFFFAOYSA-N 4-chloro-1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1F DIAWBHLTWNWYGR-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012025 fluorinating agent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical class [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 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
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
本発明は、活性ハロゲン含有化合物の存在下
に、クロロニトロベンゼン誘導体を金属フルオラ
イドによりＦ化し、２−フルオロニトロベンゼン
誘導体を得る方法に関する。
クロロニトロベンゼン誘導体を、ジメチルスル
ホキサイド（DMSO）等の非プロトン性極性溶
媒中で、弗化カリウム等の金属フルオライドと反
応させフルオロニトロベンゼン誘導体を得る際、
塩素がニトロ基のオルト位にある場合は、パラ位
にある場合に比べ、フツ素化反応収率が低いこと
が知られている。
塩素とニトロ基がオルト位に隣接した場合、ニ
トロ基が脱離し易く、ニトロ基が脱離すると
KNO2が生成し、KNO2やその分解物であるK2O
がフツ素化反応に悪影響を及ぼすため、収率が低
いと考えられている。すなわち、K2Oは原料及び
生成物と反応し、カリウムフエノキサイド誘導体
を与え、このカリウムフエノキサイド誘導体はさ
らに原料及び生成物と反応し、ジフエニルエーテ
ルタイプの生成物を与え、収率低下となると考え
られている。
本発明者等は、このような副反応を抑制し好収
率でクロロニトロベンゼン誘導体からフルオロニ
トロベンゼン誘導体を得る方法について、鋭意研
究を積み重ねたところ、活性ハロゲン含有化合物
の存在下にフツ素化反応を行なうことが効果的で
あることを見い出すに至つた。すなわち本発明は
下記一般式（）で表わされるクロロニトロベン
ゼン誘導体を、非プロトン性極性溶媒中で活性ハ
ロゲン含有化合物の存在下に金属フルオライドと
反応させ、下記一般式（）で表わされる２−フ
ルオロニトロベンゼン誘導体を得ることを特徴と
する２−フルオロニトロベンゼン誘導体の製造方
法に関するものである。
（式中、X1はCl又はＨ、X2はＦ又はＨ、Ｙ、Ｚ
はCl、NO2、又はＨを示す。）
本発明におけるクロロニトロベンゼン誘導体
は、前記一般式（）で表わされ、オルト位に隣
接した塩素とニトロ基を少なくとも１個所有する
化合物である。前記一般式（）で表わされフル
オロニトロベンゼン誘導体は、クロロニトロベン
ゼン誘導体におけるニトロ基に隣接した塩素が弗
素に置換した化合物であり、具体的な反応例は以
下の通りである。
The present invention relates to a method for obtaining a 2-fluoronitrobenzene derivative by converting a chloronitrobenzene derivative to F with a metal fluoride in the presence of an active halogen-containing compound. When reacting a chloronitrobenzene derivative with a metal fluoride such as potassium fluoride in an aprotic polar solvent such as dimethyl sulfoxide (DMSO) to obtain a fluoronitrobenzene derivative,
It is known that when chlorine is at the ortho position of the nitro group, the fluorination reaction yield is lower than when it is at the para position. When chlorine and a nitro group are adjacent to each other at the ortho position, the nitro group is likely to leave, and when the nitro group leaves,
KNO 2 is generated, KNO 2 and its decomposition product K 2 O
is thought to have a negative effect on the fluorination reaction, resulting in low yields. That is, K 2 O reacts with the raw material and product to give a potassium phenoxide derivative, which further reacts with the raw material and product to give a diphenyl ether type product, and the yield It is thought that there will be a decline. The present inventors have conducted intensive research on a method for suppressing such side reactions and obtaining fluoronitrobenzene derivatives from chloronitrobenzene derivatives in good yields, and have found that a fluorination reaction is carried out in the presence of an active halogen-containing compound. I have come to find that doing so is effective. That is, the present invention reacts a chloronitrobenzene derivative represented by the following general formula () with a metal fluoride in an aprotic polar solvent in the presence of an active halogen-containing compound to obtain 2-fluoronitrobenzene represented by the following general formula (). The present invention relates to a method for producing a 2-fluoronitrobenzene derivative, which is characterized in that the derivative is obtained. (In the formula, X 1 is Cl or H, X 2 is F or H, Y, Z
represents Cl, NO 2 or H. ) The chloronitrobenzene derivative in the present invention is a compound represented by the above general formula () and having at least one chlorine and nitro group adjacent to the ortho position. The fluoronitrobenzene derivative represented by the general formula () is a compound in which the chlorine adjacent to the nitro group in the chloronitrobenzene derivative is replaced with fluorine, and specific reaction examples are as follows.
【表】【table】
【表】【table】
【表】
反応溶媒である非プロトン性極性溶媒として
は、例えばアセトニトリル、ジメチルホルムアミ
ド、ジメチルスルホキサイド、スルホラン、Ｎ−
メチル−２−ピロリドン、Ｎ−シクロヘキシル−
２−ピロリドン、ヘキサメチルホスホルトリアミ
ド、１，３−ジメチル−２−イミダゾリジノン等
が挙げられ、特にスルホラン、ジメチルスルホキ
サイドが好ましい。溶媒の使用量は特に限定され
ないが、出発原料のクロロニトロベンゼン誘導体
に対して重量部で0.2〜20倍量好ましくは１〜５
倍量が適当である。弗素化剤としての金属フルオ
ライドとしては、KF、RbF、CsF等が好ましく、
その使用量はクロロニトロベンゼン誘導体中の弗
素置換すべき塩素基が弗素に置換するために必要
な反応理論量及び活性ハロゲン含有化合物が弗素
化されるのに必要な反応理論量の0.5倍〜10倍、
好ましくは1.1〜２倍が適当である。
ニトロ基に対してオルト位に隣接する塩素の弗
素置換反応を促進し、かつ副反応を抑制するため
に、活性ハロゲン含有化合物の存在は効果的であ
る。好ましい活性ハロゲン含有化合物は、下記一
般式（）〜（）で表される化合物を挙げるこ
とができ、特にフタル酸クロライドが好ましい。
RCOA ………（）
RSO2A ………（）
（但し、式中Ｒはアルキル基、ＡはCl、Br、Ｆ
等のハロゲン原子）
活性ハロゲン含有化合物の添加量は、出発原料
のクロロニトロベンゼン誘導体100重量部に対し
１〜100重量部、好ましくは５〜40重量部の範囲
から選定すればよい。
本発明の反応温度、時間あるいは圧力等の反応
条件は適宜最適な条件を選定すればよいが、およ
そ100〜250℃の温度、１〜20時間の反応時間及び
１〜10Kg／cm2の圧力で実施し得る。本発明に従え
ば、農医薬中間体の原料として有用な２−フルオ
ロニトロベンゼン誘導体を好収率で得ることがで
きる。
以下、本発明の実施例について、さらに具体的
に説明する。
実施例 １
200c.c.のガラス製反応器に、２−クロロニトロ
ベンゼン31.5ｇ、乾燥KF23.2ｇ、フタル酸クロ
ライド8.1ｇ、およびスルホラン80c.c.を入れ、210
℃で10時間反応させた。反応液をガスクロマトグ
ラフイで分析した処、原料の反応率85％、２−フ
ルオロニトロベンゼンへの選択率87％であつた。
比較例 １
フタル酸クロライドを添加しないこと以外、実
施例１と同様の条件で反応を行なつた処、原料の
反応率89％、２−フルオロニトロベンゼンへの選
択率61％であつた。
実施例 ２
200c.c.のガラス製反応器に、２，３−ジクロロ
ニトロベンゼン38.4ｇ、乾燥KF23.2ｇ、フタル
酸クロライド8.1ｇ、およびスルホラン80c.c.を入
れ、190℃で11時間反応させた。反応液をガスク
ロマトグラフイで分析した処、原料の反応率84
％、３−クロロ−２−フルオロニトロベンゼンへ
の選択率88％であつた。
比較例 ２
フタル酸クロライドを添加しないこと以外、実
施例１と同様の条件で反応を行なつた処、原料の
反応率87％、３−クロロ−２−フルオロニトロベ
ンゼンへの選択率58％であつた。
実施例 ３〜６
実施例２と同様な条件でフタル酸クロライドの
代りに種々の活性ハロゲン含有化合物を加えて反
応を行なつた結果を下表に示す。[Table] Examples of aprotic polar solvents used as reaction solvents include acetonitrile, dimethylformamide, dimethyl sulfoxide, sulfolane, N-
Methyl-2-pyrrolidone, N-cyclohexyl-
Examples include 2-pyrrolidone, hexamethylphosphortriamide, 1,3-dimethyl-2-imidazolidinone, and particularly preferred are sulfolane and dimethylsulfoxide. The amount of the solvent used is not particularly limited, but is preferably 0.2 to 20 parts by weight, preferably 1 to 5 parts by weight, relative to the starting material chloronitrobenzene derivative.
Double the amount is appropriate. As the metal fluoride as a fluorinating agent, KF, RbF, CsF, etc. are preferable.
The amount used is 0.5 to 10 times the theoretical reaction amount necessary for the chlorine group to be replaced with fluorine in the chloronitrobenzene derivative and the reaction theoretical amount necessary for the active halogen-containing compound to be fluorinated. ,
Preferably, 1.1 to 2 times is appropriate. The presence of an active halogen-containing compound is effective in promoting the fluorine substitution reaction of chlorine adjacent to the ortho position to the nitro group and suppressing side reactions. Preferred active halogen-containing compounds include compounds represented by the following general formulas () to (), with phthaloyl chloride being particularly preferred. RCOA ………() RSO 2 A ………() (However, in the formula, R is an alkyl group, A is Cl, Br, F
The amount of the active halogen-containing compound to be added may be selected from the range of 1 to 100 parts by weight, preferably 5 to 40 parts by weight, based on 100 parts by weight of the chloronitrobenzene derivative as the starting material. The reaction conditions of the present invention, such as reaction temperature, time, and pressure, may be selected as appropriate, but a temperature of approximately 100 to 250°C, a reaction time of 1 to 20 hours, and a pressure of 1 to 10 Kg/cm 2 are suitable. It can be implemented. According to the present invention, a 2-fluoronitrobenzene derivative useful as a raw material for agricultural and pharmaceutical intermediates can be obtained in good yield. Examples of the present invention will be described in more detail below. Example 1 31.5 g of 2-chloronitrobenzene, 23.2 g of dry KF, 8.1 g of phthaloyl chloride, and 80 c.c. of sulfolane were placed in a 200 c.c. glass reactor.
The reaction was carried out at ℃ for 10 hours. Analysis of the reaction solution by gas chromatography showed that the reaction rate of the raw materials was 85% and the selectivity to 2-fluoronitrobenzene was 87%. Comparative Example 1 A reaction was carried out under the same conditions as in Example 1 except that phthalyl chloride was not added, and the reaction rate of the raw material was 89% and the selectivity to 2-fluoronitrobenzene was 61%. Example 2 38.4 g of 2,3-dichloronitrobenzene, 23.2 g of dry KF, 8.1 g of phthaloyl chloride, and 80 c.c. of sulfolane were placed in a 200 c.c. glass reactor and reacted at 190°C for 11 hours. Ta. When the reaction solution was analyzed by gas chromatography, the reaction rate of the raw materials was 84.
%, and the selectivity to 3-chloro-2-fluoronitrobenzene was 88%. Comparative Example 2 A reaction was carried out under the same conditions as in Example 1 except that phthalyl chloride was not added, and the reaction rate of the raw material was 87%, the selectivity to 3-chloro-2-fluoronitrobenzene was 58%, and Ta. Examples 3 to 6 Reactions were carried out under the same conditions as in Example 2 except that various active halogen-containing compounds were added in place of phthalyl chloride. The results are shown in the table below.
【表】【table】
【表】
実施例 ７
200c.c.のガラス製反応器に、２，５−ジクロロ
ニトロベンゼン38.4ｇ、乾燥KF23.2ｇ、フタル
酸クロライドを10ｇ、およびジメチルスルホキシ
ド80c.c.を入れ、190℃で10時間反応させた。反応
液を分析した処、原料の反応率78％、５−クロロ
−２−フルオロニトロベンゼンへの選択率86％で
あつた。
実施例 ８
200c.c.のガラス製反応器に、１−クロロ−２，
４−ジニトロベンゼン30.4ｇ、乾燥KF21ｇ、フ
タル酸クロライド６ｇ、およびスルホラン80c.c.を
入れ、180℃で10時間反応させた。反応液を分析
した処、１−フルオロ−２，４−ジニトロベンゼ
ンの収率95％であつた。[Table] Example 7 38.4 g of 2,5-dichloronitrobenzene, 23.2 g of dry KF, 10 g of phthalic acid chloride, and 80 c.c. of dimethyl sulfoxide were placed in a 200 c.c. glass reactor, and the mixture was heated at 190°C. The reaction was allowed to proceed for 10 hours. Analysis of the reaction solution revealed that the reaction rate of the raw materials was 78% and the selectivity to 5-chloro-2-fluoronitrobenzene was 86%. Example 8 In a 200 c.c. glass reactor, 1-chloro-2,
30.4 g of 4-dinitrobenzene, 21 g of dry KF, 6 g of phthaloyl chloride, and 80 c.c. of sulfolane were added and reacted at 180°C for 10 hours. Analysis of the reaction solution revealed that the yield of 1-fluoro-2,4-dinitrobenzene was 95%.
Claims (1)
ベンゼン誘導体を、非プロトン性極性溶媒中で、
活性ハロゲン含有化合物の存在下に、金属フルオ
ライドと反応させ、下記一般式（）で表わされ
る２−フルオロニトロベンゼン誘導体を得ること
を特徴とする２−フルオロニトロベンゼン誘導体
の製造方法。 （式中、X1はCl又はＨ、X2はＦ又はＨ、Ｙ、Ｚ
はCl、NO2、又はＨを示す。）[Claims] 1. A chloronitrobenzene derivative represented by the following general formula () in an aprotic polar solvent,
A method for producing a 2-fluoronitrobenzene derivative, which comprises reacting with a metal fluoride in the presence of an active halogen-containing compound to obtain a 2-fluoronitrobenzene derivative represented by the following general formula (). (In the formula, X 1 is Cl or H, X 2 is F or H, Y, Z
represents Cl, NO 2 or H. )
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59090200A JPS60237051A (en) | 1984-05-08 | 1984-05-08 | Preparation of 2-fluoronitrobenzene derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59090200A JPS60237051A (en) | 1984-05-08 | 1984-05-08 | Preparation of 2-fluoronitrobenzene derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60237051A JPS60237051A (en) | 1985-11-25 |
| JPS6350339B2 true JPS6350339B2 (en) | 1988-10-07 |
Family
ID=13991840
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59090200A Granted JPS60237051A (en) | 1984-05-08 | 1984-05-08 | Preparation of 2-fluoronitrobenzene derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60237051A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3032883U (en) * | 1996-06-26 | 1997-01-17 | 淳 高島 | Portable night light with fragrance function |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0676343B2 (en) * | 1984-06-20 | 1994-09-28 | 株式会社トーケムプロダクツ | Novel method for producing fluorinated aromatic compounds |
| JP7123958B2 (en) | 2019-02-15 | 2022-08-23 | 福建永晶科技股▲ふん▼有限公司 | New production method for fluoroaryl compounds and their derivatives |
-
1984
- 1984-05-08 JP JP59090200A patent/JPS60237051A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3032883U (en) * | 1996-06-26 | 1997-01-17 | 淳 高島 | Portable night light with fragrance function |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60237051A (en) | 1985-11-25 |
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