JPH03240758A - Isolation of 3-n-cyclohexylaminophenol - Google Patents
Isolation of 3-n-cyclohexylaminophenolInfo
- Publication number
- JPH03240758A JPH03240758A JP3617990A JP3617990A JPH03240758A JP H03240758 A JPH03240758 A JP H03240758A JP 3617990 A JP3617990 A JP 3617990A JP 3617990 A JP3617990 A JP 3617990A JP H03240758 A JPH03240758 A JP H03240758A
- Authority
- JP
- Japan
- Prior art keywords
- cyclohexylaminophenol
- resorcinol
- reaction
- cyclohexylamine
- produced
- 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
- 238000002955 isolation Methods 0.000 title description 3
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims abstract description 30
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims description 15
- NQTSBOHCYASAMX-UHFFFAOYSA-N 2-(cyclohexylamino)phenol Chemical compound OC1=CC=CC=C1NC1CCCCC1 NQTSBOHCYASAMX-UHFFFAOYSA-N 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 3
- 238000005406 washing Methods 0.000 abstract description 8
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract description 8
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 abstract description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 abstract description 4
- 239000011592 zinc chloride Substances 0.000 abstract description 4
- 235000005074 zinc chloride Nutrition 0.000 abstract description 4
- 239000000975 dye Substances 0.000 abstract description 3
- 239000003317 industrial substance Substances 0.000 abstract description 3
- 229910052786 argon Inorganic materials 0.000 abstract description 2
- 239000011261 inert gas Substances 0.000 abstract description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 abstract description 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 2
- 239000011541 reaction mixture Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 3
- 239000012295 chemical reaction liquid Substances 0.000 abstract 2
- 239000013462 industrial intermediate Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 2
- 238000004040 coloring Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- AUELWJRRASQDKI-UHFFFAOYSA-N cyclohexyl carbamate Chemical compound NC(=O)OC1CCCCC1 AUELWJRRASQDKI-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000007787 solid Substances 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、有機工業薬品あるいは各種色素中間体として
有用な３−Ｎ−シクロヘキシルアミノフェノールの単離
法に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a method for isolating 3-N-cyclohexylaminophenol, which is useful as an organic industrial chemical or as an intermediate for various dyes.
従来、３−Ｎ−シクロへキシルアミノフェノールは、有
機工業薬品あるいは各種色素中間体として有用であるこ
とが知られている（例えば特公昭５１−１２６２６号報
、特公開５１−２３２０４号公報）。Conventionally, 3-N-cyclohexylaminophenol has been known to be useful as an organic industrial chemical or as an intermediate for various dyes (for example, Japanese Patent Publication No. 12626/1982 and Japanese Patent Publication No. 23204/1989).
また、３−Ｎ−シクロヘキシルアミノフェノールはシク
ロヘキシルアミンとレゾルシノールとの反応により生成
することも特公昭５１−１２６２６号報に記公開れてい
る。It is also disclosed in Japanese Patent Publication No. 12626/1983 that 3-N-cyclohexylaminophenol is produced by the reaction of cyclohexylamine and resorcinol.
しかしこの特公昭５１−１２６２６号報に記公開れてい
る単離方法は、いずれも反応後、３−Ｎ−シクロヘキシ
ルアミノフェノールを含む反応混合物を水洗いすること
により残存するレゾルシノールとシクロヘキシルアミン
を取り除いた後に目的とする３−Ｎ−シクロヘキシルア
ミノフェノールを単離している。However, in the isolation method disclosed in Japanese Patent Publication No. 51-12626, remaining resorcinol and cyclohexylamine were removed by washing the reaction mixture containing 3-N-cyclohexylaminophenol with water after the reaction. Later, the desired 3-N-cyclohexylaminophenol was isolated.
この方法によると、水洗の操作によりレゾルシノールや
シクロヘキシルアごンを除くことは可能であるが、未反
応あるいは過剰のシクロヘキシルアミンが存在すると水
洗により水層がアルカリ性となるため、目的とする３−
Ｎ−シクロヘキシルアミノフェノールも水層に溶は込み
、単離収率も低い（収率約２０％）ものであった。According to this method, it is possible to remove resorcinol and cyclohexylamine by washing with water, but if there is unreacted or excess cyclohexylamine, the water layer becomes alkaline by washing with water, so that the desired 3-
N-cyclohexylaminophenol was also dissolved in the aqueous layer, and the isolation yield was low (yield about 20%).
このような点から３−Ｎ−シクロヘキシルアミノフェノ
ールを簡便にしかも高収率で単離する方法の開発が強く
望まれている。From this point of view, there is a strong desire to develop a method for isolating 3-N-cyclohexylaminophenol simply and with high yield.
本発明の課題は、従来の欠点であった上述の水洗操作を
はふいた簡便で、かつ高収率で、３−Ｎシクロへキシル
アミノフェノールを単離する方法を提供することである
。An object of the present invention is to provide a method for isolating 3-N cyclohexylaminophenol in a simple and high-yield manner that eliminates the above-mentioned water washing operation, which is a drawback of the conventional methods.
本発明者らは、上述の課題を解決するために鋭意検討し
た結果、本発明に到達した。The present inventors have arrived at the present invention as a result of intensive studies to solve the above-mentioned problems.
すなわち、本発明は、シクロヘキシルアミンとレゾルシ
ノールとの反応により生成する３−Ｎシクロへキシルア
ミノフェノールを反応液から直接蒸留により単離するこ
とを特徴とする３ −Ｎ−シクロヘキシルアミノフェノ
ールの単離法である。That is, the present invention provides a method for isolating 3-N-cyclohexylaminophenol, which is characterized in that 3-N-cyclohexylaminophenol produced by the reaction of cyclohexylamine and resorcinol is isolated from the reaction solution by direct distillation. It is.
レゾルシノールとシクロヘキシルアミンとより３−Ｎ−
シクロへキシルアミノフェノールを生成する方法におい
て、レゾルシノールとシクロヘキシルアミンとの量は、
レゾルシノール１モルに対し、シクロへキジルアξンは
０．８〜２モルの範囲で使用できるが、１〜２モルの範
囲で使用するのが好ましい０反応温度は８０〜２００°
Ｃの範囲で行なうのが好ましく、１３０〜２００°Ｃの
範囲で行なうのがより好ましい、なお、この反応の際に
少量の塩化亜鉛や塩化マグネシウムを存在させると反応
を促進させることができる。反応液の着色を防止するに
は反応は窒素やアルゴン等の不活性ガス雰囲気中で行な
うことが好ましい。3-N- from resorcinol and cyclohexylamine
In the method for producing cyclohexylaminophenol, the amounts of resorcinol and cyclohexylamine are:
Cyclohexyluane ξ can be used in a range of 0.8 to 2 moles per mole of resorcinol, but it is preferable to use it in a range of 1 to 2 moles.The reaction temperature is 80 to 200°.
It is preferable to carry out the reaction at a temperature in the range of C, more preferably in the range of 130 to 200°C.The reaction can be accelerated by the presence of a small amount of zinc chloride or magnesium chloride during this reaction. In order to prevent coloring of the reaction solution, the reaction is preferably carried out in an atmosphere of an inert gas such as nitrogen or argon.
反応後、３−Ｎ−シクロヘキシルアミノフェノールを反
応系から直接蒸留する際には、常圧下でも蒸留は可能で
あるが、分解を伴う場合があるので減圧下で蒸留し単離
することが好ましい。When 3-N-cyclohexylaminophenol is directly distilled from the reaction system after the reaction, it is possible to distill it under normal pressure, but it may involve decomposition, so it is preferable to distill and isolate it under reduced pressure.
本発明によれば、３−Ｎ−シクロヘキシルアミノフェノ
ールを簡便にしかも高収率で単離することができる。According to the present invention, 3-N-cyclohexylaminophenol can be isolated easily and in high yield.
以下に実施例を挙げて、本発明を更に詳細に説明するが
、本発明はこれらに限定されるものではない。The present invention will be explained in more detail with reference to Examples below, but the present invention is not limited thereto.
実施例１
シクロヘキシルア旦ン４９５ｇ（５モル）とレゾルシノ
ール５５０ｇ（５モル）との混合物を１６０〜１７０″
Ｃで１２時間加熱攪拌した後、減圧蒸留し３−Ｎ−シク
ロヘキシルアミノフェノールを８１２ ｇを得た。Example 1 A mixture of 495 g (5 mol) of cyclohexyl urethane and 550 g (5 mol) of resorcinol was heated to 160 to 170 mm.
After heating and stirring at C for 12 hours, the mixture was distilled under reduced pressure to obtain 812 g of 3-N-cyclohexylaminophenol.
沸点 １８５〜１９０°Ｃ／ ９ ＋＊ｎＨｇ （収率
８５％）尚、このものを室温で放置しておくと白色の固
体に結晶化した。Boiling point: 185-190°C/9+*nHg (Yield: 85%) When this product was left to stand at room temperature, it crystallized into a white solid.
融点 ８７〜８９°Ｃ
実施例２
シクロヘキシルアミン７４３ｇ （７，５モル）とレゾ
ルシノール５５０ｇ（５モル）との混合物を１６０〜１
７０’ｃで１２時間加熱攪拌した後、減圧蒸留し３Ｎ−
シクロへキシルアミノフェノールを８３０ｇを得た。Melting point 87-89°C Example 2 A mixture of 743 g (7.5 mol) of cyclohexylamine and 550 g (5 mol) of resorcinol was
After heating and stirring at 70'C for 12 hours, distillation was carried out under reduced pressure to obtain 3N-
830 g of cyclohexylaminophenol was obtained.
沸点 １８５〜１９０°Ｃ／、９ ｍｎ＋Ｈｇ （収率
８７％）実施例３
シクロヘキシルアミン４９５ｇ（５モル）とレゾルシノ
ール５５０ｇ（５モル）及び無水塩化亜鉛２０ｇの混合
物を１６０〜１７０℃で８時間加熱攪拌した後、減圧蒸
留し３−Ｎ−シクロへキシルアミノフェノールを８２０
ｇを得た。Boiling point: 185-190°C/, 9 mn+Hg (yield: 87%) Example 3 A mixture of 495 g (5 mol) of cyclohexylamine, 550 g (5 mol) of resorcinol, and 20 g of anhydrous zinc chloride was heated and stirred at 160-170° C. for 8 hours. After that, 3-N-cyclohexylaminophenol was distilled under reduced pressure to give 820%
I got g.
沸点 １８５〜１９０’Ｃ／ ９ ｍｍＨｇ （収率８
６％）次に、比較例として反応液を水洗した後に３Ｎ−
シクロヘキシルアミノフェノールを単離する方法を挙げ
る。Boiling point 185-190'C/9 mmHg (yield 8
6%) Next, as a comparative example, after washing the reaction solution with water, 3N-
A method for isolating cyclohexylaminophenol is listed.
比較例１
シクロヘキシルアミン４９５ｇ（５モル）とレゾルシノ
ール５５０ｇ（５モル）との混合物を１６０〜１７０°
Ｃで１２時間加熱攪拌し、室温にまで冷却後、トルエン
２１！、を加え、トルエン層を１ｆｆｉの水で４回水洗
後、トルエン層を分離し、減圧蒸留すると３−Ｎ−シク
ロへキシルアミノフェノール１９０ ｇが得られた。Comparative Example 1 A mixture of 495 g (5 mol) of cyclohexylamine and 550 g (5 mol) of resorcinol was heated at 160 to 170°
After heating and stirring at C for 12 hours and cooling to room temperature, toluene 21! After washing the toluene layer four times with 1ffi of water, the toluene layer was separated and distilled under reduced pressure to obtain 190 g of 3-N-cyclohexylaminophenol.
沸点 １８５〜１９０°Ｃ／ ９ ｍｍＨｇ （収率２
０％）比較例２
シクロヘキシルアミン４９５ｇ’（５モル）とレゾルシ
ノール５５０ｇ（５モル）及び無水塩化亜鉛２０ｇの混
合物を１６０〜１７０°Ｃで８時間加熱攪拌し、室温に
まで冷却後、トルエン２Ｎを加え、トルエン層を１ｆｆ
ｉの水で４回水洗後、トルエン層を分離し、減圧草留す
ると３−Ｎ−シクロへキシルアミノフェノールが２００
ｇ得られた。Boiling point 185-190°C/9 mmHg (yield 2
0%) Comparative Example 2 A mixture of 495 g' (5 moles) of cyclohexylamine, 550 g (5 moles) of resorcinol, and 20 g of anhydrous zinc chloride was heated and stirred at 160 to 170°C for 8 hours, and after cooling to room temperature, 2N toluene was added. Add 1ff of toluene layer
After washing with water 4 times, the toluene layer was separated and distilled under reduced pressure to obtain 200% of 3-N-cyclohexylaminophenol.
g was obtained.
Claims (1)
より生成する３−Ｎシクロヘキシルアミノフェノールを
反応液から直接、蒸留により単離することを特徴とする
３−Ｎシクロヘキシルアミノフェノールの単離法。1) A method for isolating 3-N cyclohexylaminophenol, which comprises isolating 3-N cyclohexylaminophenol produced by the reaction of cyclohexylamine and resorcinol directly from the reaction solution by distillation.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2036179A JP2732926B2 (en) | 1990-02-19 | 1990-02-19 | Method for isolating 3-N-cyclohexylaminophenol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2036179A JP2732926B2 (en) | 1990-02-19 | 1990-02-19 | Method for isolating 3-N-cyclohexylaminophenol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03240758A true JPH03240758A (en) | 1991-10-28 |
| JP2732926B2 JP2732926B2 (en) | 1998-03-30 |
Family
ID=12462512
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2036179A Expired - Fee Related JP2732926B2 (en) | 1990-02-19 | 1990-02-19 | Method for isolating 3-N-cyclohexylaminophenol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2732926B2 (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0399042A (en) * | 1989-09-13 | 1991-04-24 | Mitsui Petrochem Ind Ltd | Production of n-substituted aminophenols |
-
1990
- 1990-02-19 JP JP2036179A patent/JP2732926B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0399042A (en) * | 1989-09-13 | 1991-04-24 | Mitsui Petrochem Ind Ltd | Production of n-substituted aminophenols |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2732926B2 (en) | 1998-03-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |