JPS6261956A - Prevention of coloring of aminophenol - Google Patents
Prevention of coloring of aminophenolInfo
- Publication number
- JPS6261956A JPS6261956A JP20285885A JP20285885A JPS6261956A JP S6261956 A JPS6261956 A JP S6261956A JP 20285885 A JP20285885 A JP 20285885A JP 20285885 A JP20285885 A JP 20285885A JP S6261956 A JPS6261956 A JP S6261956A
- Authority
- JP
- Japan
- Prior art keywords
- aminophenols
- aminophenol
- acidic
- coloring
- added
- 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
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） アミノフェノール類は、農薬、医薬中間原料。[Detailed description of the invention] (Industrial application field) Aminophenols are intermediate raw materials for agricultural chemicals and pharmaceuticals.
感熱・感圧記録紙用染料、キサンチン系染料、及び蛍光
染料用原料等として工業的に極めて有用な化合物である
。It is an extremely useful compound industrially as a raw material for heat- and pressure-sensitive recording paper dyes, xanthine dyes, and fluorescent dyes.
（従来の技術）
アミノフェノール類は、保存中（こ、酸化等の作用によ
り、保存中に経時着色することは周知であり、このため
に商品価値を下げたり、使用に当って不都合を来たすこ
とがあった。(Prior art) It is well known that aminophenols become discolored over time during storage (due to the effects of oxidation, etc.). was there.
アミノフェノール類の経時着色を防止する方法として、
特開昭５１−１１７２２号公報によれば亜硫酸ガス気流
下にアミノフェノール類を蒸留する方法が提案されてい
るが、該方法で用いる亜硫酸ガスが微量とは云え、製品
に若干の異臭が認められると共に、亜硫酸ガス自体が有
毒であるという欠点を有している。一方、特開昭５４−
４４６２２号公報に於いては、芳香族ジアミン類に一酸
化窒素を存在させる方法を提案しているが、該方法も、
前記方法と同様な欠点を有して（・る。さらに、芳香族
ジアミン類に限定されてはいるが、特開昭４９−３１６
２８号公報に於いて、還元性イオウ化合物をを添加する
方法が提案されている。還元性イオウ。As a method to prevent aminophenols from discoloring over time,
According to JP-A No. 51-11722, a method of distilling aminophenols under a stream of sulfur dioxide gas is proposed, but although the amount of sulfur dioxide gas used in this method is small, a slight off-odor is observed in the product. Additionally, sulfur dioxide gas itself has the disadvantage of being toxic. On the other hand, Japanese Unexamined Patent Publication No. 1973-
44622 proposes a method in which nitrogen monoxide is present in aromatic diamines, but this method also
It has the same drawbacks as the above method.Furthermore, although it is limited to aromatic diamines, JP-A-49-316
No. 28 proposes a method of adding a reducing sulfur compound. Reducing sulfur.
化合物として、単体イオウ、アルカリ金属の硫化物、酸
性硫化物、酸性亜硫酸塩、チオ硫酸塩等が例示されてい
るが、該化合物は、いずれも芳香族ジアミン類に限定さ
れるものであり、アミノフェノール類に適用されるとい
う記載はない。Examples of compounds include elemental sulfur, alkali metal sulfides, acid sulfides, acid sulfites, thiosulfates, etc., but these compounds are all limited to aromatic diamines; There is no mention that it applies to phenols.
（発明が解決しようとする問題点） 本発明は、有毒なガス類の使用を避け、かつ。(Problem to be solved by the invention) The present invention avoids the use of toxic gases and.
取扱いが容易な着色防止作用を有する添加剤を見い出し
、アミノフェノール類の着色防止を図ることである。The objective is to find an additive that is easy to handle and has an anti-coloration effect, and to prevent aminophenols from coloring.
（問題点を解決するだめの手段）
本発明者らは、アミノフェノール類の着色防止法につい
て鋭意検討した結果、酸性亜硫酸塩をアミノフェノール
類に少量添加することにより、アミノフェノール類の経
時着色を防止する効果のあることを発見した。即ち２本
発明は、アミノフェノール類に１種または２種以上の酸
性亜硫酸塩を０．０００５〜０．１重量％添加すること
を特徴とするアミノフェノール類の着色防止法である。(Means to Solve the Problem) As a result of intensive studies on methods for preventing coloration of aminophenols, the present inventors discovered that by adding a small amount of acidic sulfite to aminophenols, coloration of aminophenols could be prevented over time. We have discovered that it is effective in preventing That is, the present invention is a method for preventing discoloration of aminophenols, which is characterized by adding 0.0005 to 0.1% by weight of one or more acidic sulfites to aminophenols.
酸性亜硫酸塩は、特開昭４９−３１６２８号公報に例示
される還元性イオウ化合物ではあるが、該特許に例示さ
れる還元性イオウ化合物、全てが、アミノフェノール類
の着色防止に効果があるのではなく、還元性イオウ化合
物の中の酸性亜硫酸塩のみが、特異的に９着色防止作用
を持つことを見い出したものである。Acidic sulfites are reducing sulfur compounds as exemplified in JP-A No. 49-31628, but all of the reducing sulfur compounds exemplified in the patent are effective in preventing coloration of aminophenols. Rather, it was discovered that only acidic sulfites among reducing sulfur compounds have a specific coloration prevention effect.
アミノフェノール類としては１ｍ−７ミノフエノール、
ｐ−アミノフェノール、及び０−アミノフェノールがあ
げられる。これらアミノフェノール類は、ニトロベンゼ
ンからのアルカリフー−ジョン法、及び２価フーノール
類のアミノ化法によるといった製造法の差による制限は
ない。As aminophenols, 1m-7 minophenol,
Examples include p-aminophenol and 0-aminophenol. These aminophenols are not limited by the difference in production methods, such as the alkali fusion method from nitrobenzene and the amination method of divalent funols.
一方、酸性亜硫酸塩としては、酸性亜硫酸アンモニウム
、酸性亜硫酸ナトリウム、酸性亜硫酸カリウム、酸性亜
硫酸力ルンウムが選ばれるが、特に。On the other hand, as the acidic sulfite, acidic ammonium sulfite, acidic sodium sulfite, acidic potassium sulfite, and acidic sulfite are particularly selected.
酸性亜硫酸ナトリウム、酸性亜硫酸カリウムが好ましい
。Acidic sodium sulfite and acidic potassium sulfite are preferred.
一般にその添加量は９通常０．０００５〜Ｏ，１重量％
の範囲で用いられるが、特に好ましくは０．００１〜０
．Ｏ５重量％の範囲である。添加量が０．０００５重量
％未満では着色防止効果は無く、また、０．１重量％を
越えて添加することは、アミノフェノール類の純度低下
を招来するので製品規格面での問題を生じ好ましくない
。添加方法としては、特に制限はなく。Generally, the amount added is 9 usually 0.0005 to O, 1% by weight.
It is particularly preferably used in the range of 0.001 to 0.
．． It is in the range of O5% by weight. If the amount added is less than 0.0005% by weight, there will be no coloring prevention effect, and if it is added in excess of 0.1% by weight, the purity of the aminophenols will decrease, resulting in problems in terms of product specifications, so it is preferable. do not have. There are no particular restrictions on the method of addition.
酸性亜硫酸塩類は、固体粉末として添加してもよく、又
、水溶液などの液状で添加してもよい。この際、各々酸
性亜硫酸塩類は、単独でもまた各々。Acidic sulfites may be added in the form of solid powder or in liquid form such as an aqueous solution. At this time, each acidic sulfite may be used alone or individually.
２種以上の酸性亜硫酸塩類を混合して用いてもよい。A mixture of two or more types of acidic sulfites may be used.
次に１本発明を実施例に基づいて詳細に説明する。Next, one embodiment of the present invention will be explained in detail based on examples.
なお１着色の評価方法は、 Ｎ２雰囲気のメタアミノフ
ェノールの溶融液に所定の添加剤を添加し、振どう後、
ステンレストレー上に、薄く固化させ。Note 1: Coloring is evaluated by adding the specified additive to the melt of meta-aminophenol in an N2 atmosphere, shaking it, and then
Let it solidify thinly on a stainless steel tray.
メタアミノフェノールのフ区−りを得、このフレークラ
室内暗所に保存し、メタアミノフェノールの着色経時変
化を調べた。また着色度の測定は。A flake of meta-aminophenol was obtained and stored in a dark room in the flake rack, and the color change of meta-aminophenol over time was examined. Also, the degree of coloration is measured.
ＨＩＴＡＣＨＩ Ｓｐｅｃｔｒｏｐｈｏｔｏｍｅｔｅｒ
で、波長４２０ｎｒｒｌの吸光度を求め下記に示す式に
従って１モル吸光度を算出し評価した。HITACHI Spectrophotometer
Then, the absorbance at a wavelength of 420 nrrl was determined, and the 1 molar absorbance was calculated and evaluated according to the formula shown below.
（吸光度） Ｘ ｔｏ。(Absorbance) X to.
（実施例）
〈実施例−Ｉ〜２．比較例−１〜３〉
−レゾルシンのアミン（ヒ反応で得たメタアミノフェノ
−／Ｉ／（こ表１で示す。(Example) <Example-I~2. Comparative Examples 1 to 3> -Amine of resorcinol (meta-aminophenol obtained by H reaction)/I/ (Table 1 shows this.
添加剤を２５重量％水溶液で添加し、室温での着色経時
変化をみた。２ケ月間の着色経時変化を図−１に示す。Additives were added as a 25% by weight aqueous solution, and changes in coloring over time were observed at room temperature. Figure 1 shows the change in color over time over two months.
図−１から明らかなごとく、比較例−３の添加剤なし、
比較例−２のＮａ２ＳＯｓ添加のものは。As is clear from Figure 1, Comparative Example 3 without additives;
Comparative Example 2 with Na2SOs added.
褐色ないし黒褐色に経度したのに対し、実施例−１のＮ
ａＨＳＯ３，実施例−２のＫＨ５Ｏ３添加のものは初期
の淡黄白色からほとんど変化が認められなかった。又、
比較例−１のＮａｚＳｚＯｓ添加のものは多少効果が認
められたもののＮａＨ８Ｏｓ、 ＫＨ８Ｏｓに比べては
なはだ不満足な結果であった。In contrast to the longitude of brown to blackish brown, the N of Example-1
In the case of aHSO3 and KH5O3 added in Example-2, almost no change was observed from the initial pale yellowish white color. or,
Comparative Example 1, in which NazSzOs was added, was somewhat effective, but the results were extremely unsatisfactory compared to NaH8Os and KH8Os.
〈実施例−３〜６．比較例−４〉
レゾルシンのアミノ化反応で得たメタアミノフェノール
をこ９表−２で示す様にＮａＮ３Ｏ３の添加量をかえて
添加し、室温での着色経時変化をみた。<Examples-3 to 6. Comparative Example 4> Meta-aminophenol obtained by the amination reaction of resorcin was added with varying amounts of NaN3O3 as shown in Table 2, and the change in coloration over time was observed at room temperature.
なおＮａＮ５Ｏ）ｓは固体粉末で添加した。２ケ月間の
着色経時変化を図−２に示す。Note that NaN5O)s was added in the form of solid powder. Figure 2 shows the change in color over time over two months.
表−１ 表−２ （発明の効果） アミノフェノール類に還元性イオウ化合物の内。Table-1 Table-2 (Effect of the invention) Among sulfur compounds that are reducible to aminophenols.
特に酸性亜硫酸塩類を添加した時に限り、アミノフェノ
ール類の経時着色防止効果が著しく、工業的に極めて２
価値ある発明である。In particular, only when acidic sulfites are added, the effect of preventing aminophenols from discoloring over time is remarkable, and industrially it is extremely
It is a valuable invention.
Claims (3)
性亜硫酸塩を、０．０００５〜０．１重量％添加するこ
とを特徴とするアミノフェノール類の着色防止法。(1) A method for preventing discoloration of aminophenols, which comprises adding 0.0005 to 0.1% by weight of one or more acidic sulfites to aminophenols.
あることを特徴とする特許請求の範囲第（１）項記載の
アミノフェノール類の着色防止法。(2) The method for preventing discoloration of aminophenols according to claim (1), wherein the aminophenols are m-aminophenols.
硫酸カリウムであることを特徴とする特許請求の範囲第
（１）項記載のアミノフェノール類の着色防止法。(3) The method for preventing discoloration of aminophenols according to claim (1), wherein the acidic sulfite is acidic sodium sulfite or acidic potassium sulfite.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20285885A JPS6261956A (en) | 1985-09-12 | 1985-09-12 | Prevention of coloring of aminophenol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20285885A JPS6261956A (en) | 1985-09-12 | 1985-09-12 | Prevention of coloring of aminophenol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6261956A true JPS6261956A (en) | 1987-03-18 |
Family
ID=16464357
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20285885A Pending JPS6261956A (en) | 1985-09-12 | 1985-09-12 | Prevention of coloring of aminophenol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6261956A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016117719A (en) * | 2010-09-01 | 2016-06-30 | 日本曹達株式会社 | Recording material using phenolic compound |
| CN108863822A (en) * | 2017-05-09 | 2018-11-23 | 武汉武药制药有限公司 | A method of purification isoprenaline hydrochloride |
-
1985
- 1985-09-12 JP JP20285885A patent/JPS6261956A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016117719A (en) * | 2010-09-01 | 2016-06-30 | 日本曹達株式会社 | Recording material using phenolic compound |
| CN108863822A (en) * | 2017-05-09 | 2018-11-23 | 武汉武药制药有限公司 | A method of purification isoprenaline hydrochloride |
| CN108863822B (en) * | 2017-05-09 | 2021-09-21 | 武汉武药制药有限公司 | Method for refining isoproterenol hydrochloride |
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