JPH0446141A - Production of nuclear halogenated aromatic amine - Google Patents
Production of nuclear halogenated aromatic amineInfo
- Publication number
- JPH0446141A JPH0446141A JP15069590A JP15069590A JPH0446141A JP H0446141 A JPH0446141 A JP H0446141A JP 15069590 A JP15069590 A JP 15069590A JP 15069590 A JP15069590 A JP 15069590A JP H0446141 A JPH0446141 A JP H0446141A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- organic compound
- compound
- halogenated aromatic
- group
- 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.)
- Pending
Links
- 150000004982 aromatic amines Chemical class 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 6
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 claims abstract description 6
- 229910021472 group 8 element Inorganic materials 0.000 claims abstract 3
- 230000000737 periodic effect Effects 0.000 claims description 5
- -1 phosphorous organic compound Chemical class 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 17
- 150000002894 organic compounds Chemical class 0.000 abstract description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 5
- 229910052698 phosphorus Inorganic materials 0.000 abstract description 5
- 239000011574 phosphorus Substances 0.000 abstract description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract description 4
- 150000004820 halides Chemical class 0.000 abstract description 3
- 229910052751 metal Inorganic materials 0.000 abstract description 3
- 239000002184 metal Substances 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 229910052802 copper Inorganic materials 0.000 abstract description 2
- 229910052737 gold Inorganic materials 0.000 abstract description 2
- 229910052741 iridium Inorganic materials 0.000 abstract description 2
- 229910052759 nickel Inorganic materials 0.000 abstract description 2
- 229910052762 osmium Inorganic materials 0.000 abstract description 2
- 229910052763 palladium Inorganic materials 0.000 abstract description 2
- 229910052697 platinum Inorganic materials 0.000 abstract description 2
- 229910052703 rhodium Inorganic materials 0.000 abstract description 2
- 229910052707 ruthenium Inorganic materials 0.000 abstract description 2
- 229910052709 silver Inorganic materials 0.000 abstract description 2
- 229910052742 iron Inorganic materials 0.000 abstract 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 239000002994 raw material Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- 229910002090 carbon oxide Inorganic materials 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- INMZDDDQLHKGPF-UHFFFAOYSA-N 4-bromo-2-chloroaniline Chemical compound NC1=CC=C(Br)C=C1Cl INMZDDDQLHKGPF-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DYSRXWYRUJCNFI-UHFFFAOYSA-N 2,4-dibromoaniline Chemical compound NC1=CC=C(Br)C=C1Br DYSRXWYRUJCNFI-UHFFFAOYSA-N 0.000 description 1
- KQCMTOWTPBNWDB-UHFFFAOYSA-N 2,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C=C1Cl KQCMTOWTPBNWDB-UHFFFAOYSA-N 0.000 description 1
- HHWOYRKNRZSNQE-UHFFFAOYSA-N 2-bromo-4-iodoaniline Chemical compound NC1=CC=C(I)C=C1Br HHWOYRKNRZSNQE-UHFFFAOYSA-N 0.000 description 1
- MYDAOWXYGPEPJT-UHFFFAOYSA-N 2-chloro-4-iodoaniline Chemical compound NC1=CC=C(I)C=C1Cl MYDAOWXYGPEPJT-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910021604 Rhodium(III) chloride Inorganic materials 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000001495 arsenic compounds Chemical class 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- ILCQYORZHHFLNL-UHFFFAOYSA-N n-bromoaniline Chemical compound BrNC1=CC=CC=C1 ILCQYORZHHFLNL-UHFFFAOYSA-N 0.000 description 1
- 150000005181 nitrobenzenes Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002897 organic nitrogen compounds Chemical class 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、ハロゲン化アニリン等の核ハロゲン化芳香族
アミンの製造に利用できる。DETAILED DESCRIPTION OF THE INVENTION (Industrial Field of Application) The present invention can be used in the production of nuclear halogenated aromatic amines such as halogenated anilines.
（従来の技術及び発明が解決しよう“とする課題）核ハ
ロゲン化芳香族アミン、例えばハロゲン化アニリンは、
ハロゲン化ベンゼンをニトロ化した後これを還元すると
いう二段反応での製法が知られている。本発明は更に効
率的な製法即ち、−段の反応で核ハロゲン化芳香族アミ
ンを製造する方法を提供することを目的とするものであ
る。(Prior art and problems to be solved by the invention) Nuclear halogenated aromatic amines, such as halogenated aniline,
A two-step reaction method is known in which halogenated benzene is nitrated and then reduced. It is an object of the present invention to provide a more efficient production method, that is, a method for producing nuclear halogenated aromatic amines in a two-stage reaction.
（課題を解決するための手段）
本発明者は、鋭意検討の結果、出発原料として、ニトロ
基を有する芳香族化合物を用い、特定の触媒の存在下、
−酸化炭素等を用いた還元雰囲気下でハロゲン化水素酸
を反応させることにより、ニド四基の還元と芳香環のハ
ロゲン化が一段の反応で行われることを見いだし本発明
に至った。(Means for Solving the Problems) As a result of intensive studies, the present inventors used an aromatic compound having a nitro group as a starting material, and in the presence of a specific catalyst,
-We have discovered that the reduction of four nido groups and the halogenation of aromatic rings can be carried out in a single reaction by reacting hydrohalic acid in a reducing atmosphere using carbon oxide or the like, leading to the present invention.
即ち、本発明は、ニトロ基を有する芳香族化合物を、周
期律表第■族元素またはＩＢ族元素およびリン系有機化
合物からなる触媒を用い、還元雰囲気下でハロゲン化水
素酸と反応させることを特徴とする核ハロゲン化芳香族
アミンの製法である。That is, the present invention involves reacting an aromatic compound having a nitro group with a hydrohalic acid in a reducing atmosphere using a catalyst consisting of an element of Group I or Group IB of the periodic table and a phosphorus organic compound. This is a characteristic method for producing nuclear halogenated aromatic amines.
本反応で用いる周期律表第■族元素とは、Ｆｅ。The Group Ⅰ element of the periodic table used in this reaction is Fe.
Ｃｏ 、 Ｎｉ 、 Ｒｕ 、 Ｒｈ 、 Ｐｄ 、
Ｏｓ 、 Ｉｒ 、 Ｐｔである。これらの遷移金属触
媒は、金属、ハロゲン化物、有機化合物、酸化物等の形
で加えることができる。また、周期律表第１Ｂ族元素は
、Ｃｕ 、 Ａｇ 、 Ａｕであり金属。Co, Ni, Ru, Rh, Pd,
They are Os, Ir, and Pt. These transition metal catalysts can be added in the form of metals, halides, organic compounds, oxides, and the like. In addition, the elements of Group 1B of the periodic table are Cu, Ag, and Au, which are metals.
ハロゲン化物、有機化合物、酸化物等の形で加えること
ができる。有機燐化合物、有機硫黄化合物。It can be added in the form of halides, organic compounds, oxides, etc. Organophosphorus compounds, organosulfur compounds.
有機窒素化合物、有機ひ素化合物等が触媒配位子として
配位した形の遷移金属触媒を用いてもよい。加える量は
、原料に対して１７１〜１／１００００モル倍好ましく
は１１１０〜１１５００モル倍である。A transition metal catalyst in which an organic nitrogen compound, an organic arsenic compound, or the like is coordinated as a catalyst ligand may be used. The amount added is 171 to 1/10,000 times, preferably 1,110 to 11,500 times by mole relative to the raw material.
リン系有機化合物としては、分子中に３価のリン原子を
１個または２個以上含有する化合物があげられ、例えば
トリアルキルホスフィン、トリアリールホスフィン、ト
リシクロアルキルホスフィン ダイホスフィン等が使用
できる。これらのリン系有機化合物は、前記の周期律表
第■族元素またはＩＢ族元素に対して１〜１００モル倍
、好ましくは１〜１０モル倍使用できる。Examples of the phosphorus-based organic compound include compounds containing one or more trivalent phosphorus atoms in the molecule, such as trialkylphosphine, triarylphosphine, tricycloalkylphosphine, diphosphine, and the like. These phosphorus-based organic compounds can be used 1 to 100 times, preferably 1 to 10 times by mole, the Group I element or IB group element of the periodic table.
原料のニトロ基を有する芳香族化合物は、少なくとも芳
香環に１つ以上のニトロ基をもつ芳香族化合物であり、
本性によって合成できる化合物の例としては、０−クロ
ルアニリン、０−ブロムアニリン、０−ヨードアニリン
、ｐ−ハロゲン化ニトロベンゼンを原料とした場合には
、２，４−ジクロロアニリン。The aromatic compound having a nitro group as a raw material is an aromatic compound having at least one nitro group in an aromatic ring,
Examples of compounds that can be synthesized depending on their properties include 0-chloroaniline, 0-bromoaniline, 0-iodoaniline, and 2,4-dichloroaniline when p-halogenated nitrobenzene is used as a raw material.
２−クロロ−４−ブロモアニリン、２−クロロ−４−ヨ
ー・ドアニリン、２，４−ジブロモアニリン、２−クロ
ロ−４−ブロモアニリン、２−ヨード−本ブロモアニリ
ン、２，４−ショートアニリン、２−ブロモ−４−ヨー
ドアニリン等が合成できる。2-chloro-4-bromoaniline, 2-chloro-4-iodoaniline, 2,4-dibromoaniline, 2-chloro-4-bromoaniline, 2-iodo-real bromoaniline, 2,4-short aniline, 2-bromo-4-iodoaniline and the like can be synthesized.
上記以外にも使用する原料をかえることによって種々の
ハロゲン化アニリンの合成が可能である。In addition to the above, various halogenated anilines can be synthesized by changing the raw materials used.
本発明に用いる塩化水素酸、ヨウ化水素酸、臭化水素酸
等のハロゲン化水素酸は何％のものでもよい。しかし、
反応を速やかに進行させるために好ましくは、１％以上
のものが好ましい。１％以下の濃度では反応速度は、著
しく遅く目的の化合物の収率低下をもたらす。また、還
元雰囲気を構成するためには、−酸化炭素が好適に用い
られる。The hydrohalic acid such as hydrochloric acid, hydroiodic acid, and hydrobromic acid used in the present invention may be in any percentage. but,
In order to allow the reaction to proceed rapidly, the content is preferably 1% or more. At concentrations below 1%, the reaction rate is significantly slow resulting in a decrease in the yield of the desired compound. Furthermore, -carbon oxide is suitably used to form a reducing atmosphere.
この−酸化炭素は、水素ガスと混合して用いてもよい。This carbon oxide may be used in combination with hydrogen gas.
また、窒素、二酸化炭素、ヘリウム、アルゴン等の不活
性ガスを共存させることもできる。反応は、無溶媒系で
もよいが、反応を円滑に進めるため通常溶媒が用いられ
る。用いる溶媒とじては、ケトン類、例えば、メチルエ
チルケトン、アセトン、２−ペンタノン、３−ペンタノ
ン、アセトフェノン、芳香族炭化水素類、例えば、ベン
ゼン、トルエン、ハロゲン化ベンゼン、環状エーテル類
、例えば、テトラヒドロフラン、ジオキサンのような溶
媒が望ましい。この溶媒の使用量は原料に対して１７１
０〜１０モル倍程度が望ま上程。反応温度は、３０°Ｃ
〜２００°Ｃ好ましくは、７０°Ｃ〜１７０°Ｃの範囲
である。上記の物質を、例えば、オートクレーブに仕込
み反応を開始する。還元剤であるＣＯガスの圧力は、Ｉ
Ｋｇ１ｃｍ２〜１００Ｋｇ／Ｃｍ２の範囲内で十分であ
る。具体的には、実施例により説明する。In addition, an inert gas such as nitrogen, carbon dioxide, helium, or argon can also be present. Although the reaction may be carried out without a solvent, a solvent is usually used to facilitate the reaction. Examples of solvents used include ketones such as methyl ethyl ketone, acetone, 2-pentanone, 3-pentanone, acetophenone, aromatic hydrocarbons such as benzene, toluene, halogenated benzene, and cyclic ethers such as tetrahydrofuran and dioxane. Solvents such as The amount of this solvent used is 171% of the raw material.
The desirable upper range is about 0 to 10 times the mole. Reaction temperature is 30°C
-200°C, preferably 70°C - 170°C. For example, the above substances are charged into an autoclave and the reaction is started. The pressure of CO gas, which is a reducing agent, is I
A range of Kg1cm2 to 100Kg/Cm2 is sufficient. Specifically, this will be explained using examples.
（実施例）
実施例１
３００ｃｃのオートクレーブに、ニトロベンゼン１２８
ｍｍｏｌ 、メチルエチルケトン４９４ｍｍｏｌ 、
ＰｄＣｌ２１．８ｍｍｏｌ 、 ）リフェニルホスフィ
ン５．４ｍｍｏｌ 。(Example) Example 1 In a 300cc autoclave, nitrobenzene 128
mmol, methyl ethyl ketone 494 mmol,
PdCl21.8mmol, ) Riphenylphosphine 5.4mmol.
１０％ＨＣＩ ４７ｇを添加する。オートクレーブ内を
ＣＯガスで置換したのち、７０Ｋｇ／Ｃｍ２の圧力まで
張り込む。反応は、１３０°Ｃで１時間行い反応後の粗
液をガスクロマトグラフィーで分析した結果、転化率１
００％、オルトクロルアニリン４５％、パラクロルアニ
リン３５％、アニリン１５％を得た。Add 47 g of 10% HCI. After replacing the inside of the autoclave with CO gas, the autoclave is filled to a pressure of 70 Kg/Cm2. The reaction was carried out at 130°C for 1 hour, and the crude liquid after the reaction was analyzed by gas chromatography. As a result, the conversion rate was 1.
00%, orthochloroaniline 45%, parachloroaniline 35%, and aniline 15%.
比較例１
実施例１でトリフェニルホスフィンを加えずに反応させ
た結果、転化率は０％であった。Comparative Example 1 As a result of carrying out the reaction in Example 1 without adding triphenylphosphine, the conversion rate was 0%.
実施例２
実施例１で触媒をＲｈＣｌ３に変えた以外はすべて同様
な実験を行った。その結果、転化率１０％、オルトクロ
ルアニリン５％パラクロルアニリン１％を得た。Example 2 The same experiment as in Example 1 was conducted except that the catalyst was changed to RhCl3. As a result, a conversion rate of 10% and 5% orthochloroaniline and 1% parachloroaniline were obtained.
実施例３
実施例１で触媒をＣｕＣｌ２に変えた以外はすべて同様
な実験を行った。その結果、転化率３０％、オルトクロ
ルアニリン２０％パラクロルアニリン５％、アニリン３
％を得た。Example 3 All experiments were conducted in the same manner as in Example 1 except that the catalyst was changed to CuCl2. As a result, the conversion rate was 30%, orthochloroaniline 20%, parachloroaniline 5%, aniline 3
I got %.
（発明の効果）
本発明により従来より工程の短縮された効率的な核ハロ
ゲン化芳香族アミンの製法を提供することができた。(Effects of the Invention) According to the present invention, it was possible to provide an efficient method for producing a nuclear halogenated aromatic amine with shorter steps than in the past.
Claims (1)
素または I Ｂ族元素およびリン系有機化合物からなる
触媒を用い、還元雰囲気下でハロゲン化水素酸と反応さ
せることを特徴とする核ハロゲン化芳香族アミンの製法
。Nuclear halogen characterized by reacting an aromatic compound having a nitro group with hydrohalic acid in a reducing atmosphere using a catalyst consisting of a Group VIII element or IB element of the periodic table and a phosphorous organic compound. Process for producing aromatic amines.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15069590A JPH0446141A (en) | 1990-06-08 | 1990-06-08 | Production of nuclear halogenated aromatic amine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15069590A JPH0446141A (en) | 1990-06-08 | 1990-06-08 | Production of nuclear halogenated aromatic amine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0446141A true JPH0446141A (en) | 1992-02-17 |
Family
ID=15502418
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15069590A Pending JPH0446141A (en) | 1990-06-08 | 1990-06-08 | Production of nuclear halogenated aromatic amine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0446141A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5442114A (en) * | 1993-01-29 | 1995-08-15 | Sumitomo Chemical Company, Limited | Process for producing aromatic amide compounds |
-
1990
- 1990-06-08 JP JP15069590A patent/JPH0446141A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5442114A (en) * | 1993-01-29 | 1995-08-15 | Sumitomo Chemical Company, Limited | Process for producing aromatic amide compounds |
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