JPH0450297B2 - - Google Patents
Info
- Publication number
- JPH0450297B2 JPH0450297B2 JP60275039A JP27503985A JPH0450297B2 JP H0450297 B2 JPH0450297 B2 JP H0450297B2 JP 60275039 A JP60275039 A JP 60275039A JP 27503985 A JP27503985 A JP 27503985A JP H0450297 B2 JPH0450297 B2 JP H0450297B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- phenylenediamine
- water
- amino
- present
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 13
- 229940018564 m-phenylenediamine Drugs 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 12
- 238000006460 hydrolysis reaction Methods 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 230000007062 hydrolysis Effects 0.000 claims description 6
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 claims description 4
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 7
- 238000006722 reduction reaction Methods 0.000 description 7
- ZZMRPOAHZITKBV-UHFFFAOYSA-N 3-aminocyclohex-2-en-1-one Chemical compound NC1=CC(=O)CCC1 ZZMRPOAHZITKBV-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- -1 cyclohexene-1,3-dione (dihydroresorcinol) Chemical compound 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 3
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 229960001755 resorcinol Drugs 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- 229940018563 3-aminophenol Drugs 0.000 description 1
- AEVMBQIIZGKQRB-UHFFFAOYSA-N 5-oxohexanenitrile Chemical group CC(=O)CCCC#N AEVMBQIIZGKQRB-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003905 agrochemical Chemical class 0.000 description 1
- 150000001334 alicyclic compounds Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008096 xylene Substances 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
【発明の詳細な説明】
（産業上の利用分野）
本発明は、多官能性を有する３−アミノ−２−
シクロヘキセン−１−オンの製造法に関する。Detailed Description of the Invention (Industrial Field of Application) The present invention provides polyfunctional 3-amino-2-
The present invention relates to a method for producing cyclohexen-1-one.
より詳しくは、ｍ−フエニレンジアミンを、水
および還元触媒の存在下に部分還元および加水分
解させることを特徴とする３−アミノ−２−シク
ロヘキセン−１−オンの製造法に関するものであ
る。 More specifically, the present invention relates to a method for producing 3-amino-2-cyclohexen-1-one, which comprises partially reducing and hydrolyzing m-phenylenediamine in the presence of water and a reducing catalyst.
３−アミノ−２−シクロヘキセン−１−オンは
簡単な構造にもかかわらず、分子内に炭素−炭素
二重結合、カルボニル基、アミノ基を有し、さら
にこれらがα、β不飽和ケトン、エナミン構造を
有しており、いわゆる多官能性化合物である。 Although 3-amino-2-cyclohexen-1-one has a simple structure, it has a carbon-carbon double bond, a carbonyl group, and an amino group in the molecule, and these also form α- and β-unsaturated ketones and enamines. structure, and is a so-called polyfunctional compound.
この化合物は芳香族環に脱水素してｍ−アミノ
フエノールに誘導できるのを初めとして（例え
ば、西独公開特許公報2402695号）、種々の複素還
化合物、農薬、高分子化合物等の原料として用い
ることのできる有用な化合物である。 This compound can be derived from m-aminophenol by dehydrogenating the aromatic ring (for example, West German Published Patent Application No. 2402695), and can also be used as a raw material for various heterocyclic compounds, agricultural chemicals, polymer compounds, etc. It is a useful compound that can
（従来の技術）
従来、３−アミノ−２−シクロヘキセン−１−
オンは例えば、シクロヘキセン−１，３−ジオン
（ジヒドロレゾルシン）とアンモニアから脱水縮
合により製造し得ることが知られている（ナチユ
ール ブイセン シヤフテン（Natur wissen
shaften）誌第47巻、第83頁（1960））。しかしな
がら、この方法で用いられるジヒドロレゾルシン
は、通常、ｍ−ジヒドロキシベンゼン（レジルシ
ン）の部分還元により製造され、工業的には、レ
ゾルシンが高価なことと製造工程が長くなるとい
う欠点を有し、あまり有利な方法とは言えない。(Prior art) Conventionally, 3-amino-2-cyclohexene-1-
It is known that one can be produced, for example, from cyclohexene-1,3-dione (dihydroresorcinol) and ammonia by dehydration condensation (Natur Wissen).
vol. 47, p. 83 (1960)). However, the dihydroresorcin used in this method is usually produced by partial reduction of m-dihydroxybenzene (resorcin), and it has the disadvantages that resorcin is expensive and the manufacturing process is long, so it is not used industrially. I can't say it's an advantageous method.
また、５−オキソヘキサンニトリルを塩基性触
媒と有機極性溶媒の存在下に高温で環化水分解解
して３−アミノ−２−シクロヘキサン−１−オン
を得る方法が開示されているが（特開昭54−
92942号公報）選択率が低く、また、160℃以上の
高温を必要とし、製品の単離には有機極性溶媒を
除去しなければならないなど、工業的には不経済
なプロセスであると言える。 Furthermore, a method for obtaining 3-amino-2-cyclohexane-1-one by cyclization-hydrolytic decomposition of 5-oxohexanenitrile at high temperature in the presence of a basic catalyst and an organic polar solvent has been disclosed (particularly 1977-
92942)) It can be said that it is an industrially uneconomical process, as it has a low selectivity, requires high temperatures of 160°C or higher, and requires removal of the organic polar solvent to isolate the product.
（発明が解決しようとする問題点）
本発明の目的は、３−アミノ−２−シクロヘキ
ザン−１−オンを入手容易な原料を用いて、しか
も簡単な反応で製造する方法を提供することであ
る。(Problems to be Solved by the Invention) An object of the present invention is to provide a method for producing 3-amino-2-cyclohexan-1-one using easily available raw materials and by a simple reaction. be.
（問題点を解決するための手段）
本発明者等は、上記の目的を達成するため、鋭
意研究を重ねた結果、本発明に到達した。(Means for Solving the Problems) In order to achieve the above object, the inventors of the present invention have conducted intensive research and have arrived at the present invention.
すなわち、本発明はｍ−フエニレンジアミン
を、水および還元触媒の存在下に室温において水
素化し、同時に加水分解を行なわせることにより
高収率で３−アミノ−２−シクロヘキセン−１−
オンを製造する方法である。 That is, the present invention hydrogenates m-phenylenediamine at room temperature in the presence of water and a reducing catalyst, and simultaneously hydrolyzes it to produce 3-amino-2-cyclohexene-1- in high yield.
This is a method of manufacturing on.
本発明の方法に用いる原料化合物はｍ−フエニ
レンジアミンであつて、この化合物そのものを原
料として用いてもかまわないし、あるいはｍ−ジ
ニトロベンゼンやｍ−ニトロアニリンのようなベ
ンゼン誘導体を還元反応させて得られるｍ−フエ
ニレンジアミンを単離することなく引き続いて本
発明の方法に用いてもよい。 The raw material compound used in the method of the present invention is m-phenylenediamine, and this compound itself may be used as a raw material, or a benzene derivative such as m-dinitrobenzene or m-nitroaniline may be subjected to a reduction reaction. The m-phenylenediamine obtained may be used subsequently in the process of the invention without isolation.
ｍ−フエニレンジアミン以外のベンゼン誘導体
を原料として用いると、ジアミンへの還元および
さらに３−アミノ−２−シクロヘキセン−１−オ
ンへの還元と加水分解を同一の反応器中で引き続
き行うことができる。 When benzene derivatives other than m-phenylenediamine are used as raw materials, reduction to diamine and further reduction to 3-amino-2-cyclohexen-1-one and hydrolysis can be carried out sequentially in the same reactor. .
本発明の方法では還元反応および加水分解を水
または水以外の溶媒中で行うことができる。溶媒
としては、脂肪族アルコール類、例えば、メタノ
ール、エタノール、イソプロピルアルコールや芳
香族炭化水素、例えば、ベンゼン、トルエン、キ
シレン等があげられる。 In the method of the present invention, the reduction reaction and hydrolysis can be carried out in water or a solvent other than water. Examples of the solvent include aliphatic alcohols such as methanol, ethanol, and isopropyl alcohol, and aromatic hydrocarbons such as benzene, toluene, and xylene.
本発明の方法における水素化反応は還元触媒の
いずれによつても触媒作用される。 The hydrogenation reaction in the process of the invention is catalyzed by any reducing catalyst.
触媒としては、白金黒、パラジウム、ラネーニ
ツケル、コバルト等の各種の還元用触媒が使用で
きる。 As the catalyst, various reduction catalysts such as platinum black, palladium, Raney nickel, and cobalt can be used.
使用する触媒の量は任意に選べるが、ｍ−フエ
ニレンジアミンに対して、0.001〜５％の範囲で
十分である。 The amount of catalyst used can be selected arbitrarily, but a range of 0.001 to 5% based on m-phenylenediamine is sufficient.
加水分解には原料のｍ−フエニレンジアミンに
対して少なくとも等モルの水の存在が必要であ
る。 Hydrolysis requires the presence of at least equimolar amount of water to m-phenylenediamine as a raw material.
したがつて、有機溶媒中で反応を行う場合は、
加水分解に必要な水を添加する。通常、ｍ−フエ
ニレンジアミンに対して、１〜100等量の水を添
加する。 Therefore, when carrying out the reaction in an organic solvent,
Add water required for hydrolysis. Usually, 1 to 100 equivalents of water is added to m-phenylenediamine.
一方、ｍ−ジニトロベンゼンやｍ−ニトロアニ
リンのうように還元により水を生成するような化
合物を出発物質とする場合には、反応の進行によ
り生成した水が本発明の加水分解に使用されるた
め、水の系外逸散を防げば水の追加は必ずしも必
要とはしない。 On the other hand, when a compound that produces water upon reduction, such as m-dinitrobenzene or m-nitroaniline, is used as a starting material, the water produced as the reaction progresses is used for the hydrolysis of the present invention. Therefore, if water is prevented from escaping out of the system, it is not necessarily necessary to add water.
反応は常圧、加圧いずれでも良い。触媒によつ
ては過水添され、脂環式化合物、例えば、シクロ
ヘキシルジアミンのような副生物の増大を招くた
め、水素の添加量はｍ−フエニレンジアミンに対
して、ほぼ等量を用い、この量を管理することが
好ましい。加圧下での反応は、反応速度が必要な
場合に有利であり、例えば、オートクレーブなど
を用いて反応させ得る。 The reaction may be carried out at normal pressure or under increased pressure. Depending on the catalyst, perhydrogenation may occur, leading to an increase in by-products such as alicyclic compounds such as cyclohexyldiamine, so the amount of hydrogen added is approximately equal to m-phenylenediamine. It is preferable to control this amount. Reaction under pressure is advantageous when a high reaction rate is required, and the reaction can be carried out using, for example, an autoclave.
反応温度も任意に選択しうるが、室温から180
℃程度で十分であるが、室温近傍の温度が好まし
い。 The reaction temperature can also be selected arbitrarily, but ranges from room temperature to 180°C.
A temperature of about 0.degree. C. is sufficient, but a temperature near room temperature is preferable.
加水分解反応を促進するために、酢酸、ｐ−ト
ルエンスルホン酸、フエノールスルホン酸等の酸
を共存させることもできる。 In order to promote the hydrolysis reaction, acids such as acetic acid, p-toluenesulfonic acid, and phenolsulfonic acid can also be present.
この場合、使用する酸の量は、ｍ−フエニレン
ジアミンに対して0.1〜10等量である。 In this case, the amount of acid used is from 0.1 to 10 equivalents based on m-phenylenediamine.
本発明の方法は、回分式、連続式のいずれかの
方法で実施しうる。 The method of the present invention can be carried out either batchwise or continuously.
反応終了後の反応混合物から触媒を除去し、抽
出、濃縮等の方法により目的とする３−アミノ−
２−シクロヘキセン−１−オンを単離することが
できる。 After the reaction, the catalyst is removed from the reaction mixture, and the desired 3-amino-
2-Cyclohexen-1-one can be isolated.
（実施例） 以下、本発明を実施例により詳細に説明する。(Example) Hereinafter, the present invention will be explained in detail with reference to Examples.
実施例 １
200mlSUS製オートクレーブにｍ−フエニレン
ジアミン5.4ｇ、酢酸４ｇを含む水100ml、５％パ
ラジウム黒１ｇ（日本エンゲルハルト社製、高活
性Pd−Ｃ、含水品）を装入し、水素雰囲気下、
常圧で内容物を室温で10時間攪拌した。約1200ml
の水素を吸収した。反応終了後触媒を濾過し、水
層PH11に調整し、クロロホルムで抽出し、濃縮し
たところ、3.2ｇの結晶が単離された。元素分析、
NMR，IRによりこの結晶が３−アミノ−２−シ
クロヘキセン−１−オンであることを確認した。
水層も含め全反応混合物中の目的生成物はガスク
ロマトグラフイーにより80％の収率であつた。Example 1 A 200 ml SUS autoclave was charged with 100 ml of water containing 5.4 g of m-phenylenediamine, 4 g of acetic acid, and 1 g of 5% palladium black (manufactured by Nippon Engelhardt Co., Ltd., highly active Pd-C, water-containing product) and placed in a hydrogen atmosphere. under,
The contents were stirred at room temperature for 10 hours at normal pressure. Approximately 1200ml
of hydrogen was absorbed. After the reaction was completed, the catalyst was filtered, the pH of the aqueous layer was adjusted to 11, extracted with chloroform, and concentrated to isolate 3.2 g of crystals. elemental analysis,
It was confirmed by NMR and IR that this crystal was 3-amino-2-cyclohexen-1-one.
The desired product in the entire reaction mixture including the aqueous layer was found to have a yield of 80% by gas chromatography.
実施例 ２
200mlSUS製オートクレーブにｍ−ジニトロベ
ンゼン8.4ｇ、酢酸12ｇを含む水100ml、５％パラ
ジウム黒１ｇ（日本エンゲルハルト社製、高活性
Pd−Ｃ、含水品）を装入し、100Kg／cm2の水素加
圧下に内容物を室温で６時間攪拌した。反応終了
後触媒を濾過し、水層PH11に調整し、クロロホル
ムで抽出し、濃縮したところ、２ｇの結晶が単離
された。元素分析、NMR、IRによりこの結晶が
３−アミノ−２−シクロヘキセン−１−オンであ
ることを確認した。Example 2 In a 200 ml SUS autoclave, 100 ml of water containing 8.4 g of m-dinitrobenzene and 12 g of acetic acid, 1 g of 5% palladium black (manufactured by Nippon Engelhard Co., Ltd., highly active)
Pd-C, water-containing product) was charged, and the contents were stirred at room temperature for 6 hours under a hydrogen pressure of 100 Kg/cm 2 . After the reaction was completed, the catalyst was filtered, the pH of the aqueous layer was adjusted to 11, extracted with chloroform, and concentrated to isolate 2 g of crystals. This crystal was confirmed to be 3-amino-2-cyclohexen-1-one by elemental analysis, NMR, and IR.
水層も含め全反応混合物中の目的生成物はガス
クロマトグラフイーにより65％の収率であつた。 The desired product in the entire reaction mixture, including the aqueous layer, was found to have a yield of 65% by gas chromatography.
Claims (1)
媒の存在下に室温において水素化し、同時に加水
分解を行なうことを特徴とする３−アミノ−２−
シクロヘキセン−１−オンの製造法。 ２ ｍ−フエニレンジアミンがｍ−ジニトロベン
ゼンを水添反応させて得られたものを引き続き使
用するものである請求項１記載の製造法。[Claims] 3-Amino-2-, characterized in that 1 m-phenylenediamine is hydrogenated at room temperature in the presence of water and a reducing catalyst, and hydrolysis is simultaneously carried out.
Method for producing cyclohexen-1-one. 2. The production method according to claim 1, wherein the m-phenylenediamine obtained by hydrogenating m-dinitrobenzene is subsequently used.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60275039A JPS62135451A (en) | 1985-12-09 | 1985-12-09 | Production of 3-amino-2-cyclohexen-2-one |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60275039A JPS62135451A (en) | 1985-12-09 | 1985-12-09 | Production of 3-amino-2-cyclohexen-2-one |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62135451A JPS62135451A (en) | 1987-06-18 |
| JPH0450297B2 true JPH0450297B2 (en) | 1992-08-13 |
Family
ID=17550010
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60275039A Granted JPS62135451A (en) | 1985-12-09 | 1985-12-09 | Production of 3-amino-2-cyclohexen-2-one |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62135451A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5149874A (en) * | 1991-04-15 | 1992-09-22 | E. I. Du Pont De Nemours And Company | Method for manufacturing 3-amino-2-cyclohexene-1-one, and a novel polymer ingredient and its preparation |
| US5268508A (en) * | 1991-04-15 | 1993-12-07 | E. I. Du Pont De Nemours And Company | Method for manufacturing 3-amino-2-cyclohexene-1-one, and a novel polymer ingredient and its preparation |
-
1985
- 1985-12-09 JP JP60275039A patent/JPS62135451A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62135451A (en) | 1987-06-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |