JPS6042785B2 - Method for producing 1-amino-2,4-dibromanthraquinone - Google Patents
Method for producing 1-amino-2,4-dibromanthraquinoneInfo
- Publication number
- JPS6042785B2 JPS6042785B2 JP4841377A JP4841377A JPS6042785B2 JP S6042785 B2 JPS6042785 B2 JP S6042785B2 JP 4841377 A JP4841377 A JP 4841377A JP 4841377 A JP4841377 A JP 4841377A JP S6042785 B2 JPS6042785 B2 JP S6042785B2
- Authority
- JP
- Japan
- Prior art keywords
- aminoanthraquinone
- amino
- producing
- dibromanthraquinone
- sulfuric acid
- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明はアントラキノン系染料の中間体として重要な１
−アミノー２ ・ ４−ジブロムアントラキノンの工業
的に有利な製造法に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention is directed to one of the important intermediates for anthraquinone dyes.
This invention relates to an industrially advantageous method for producing -amino-2.4-dibromoanthraquinone.
１−アミノー ２ ・ ４−ジブロムアントラキノンは
古くから知られた染料用中間体であり、工業的な製造法
としてはＰＢレポートの時代からの方法として１−アミ
ノアントラキノンを濃硫酸又は発煙硫酸に溶解したのち
、大量の水に注いで１−アミノアントラキノンの微細粒
子を含む懸濁液とし、続いて塩素あるいは塩素酸ナトリ
ウムと塩酸の存在下に臭素を作用させてジブロム体とす
る方法が広く用いられている（例えば細田豊著「染料化
学」第５７２ページ）。1-Amino-2-4-dibromoanthraquinone is a dye intermediate that has been known for a long time, and the industrial method for manufacturing it, which dates back to the time of the PB report, is to dissolve 1-aminoanthraquinone in concentrated sulfuric acid or fuming sulfuric acid. A widely used method is then to pour it into a large amount of water to form a suspension containing fine particles of 1-aminoanthraquinone, and then to react with bromine in the presence of chlorine or sodium chlorate and hydrochloric acid to form the dibrome compound. (For example, "Dye Chemistry" by Yutaka Hosoda, page 572).
この方法では臭素化を円滑に進行させるために１−アミ
ノアントラキノンを一旦硫酸に溶解させ大量の水に排出
して分散させているため、反応に必須ではない硫酸を使
用しており、また特に環境規制が厳しくなつてきたため
排水処理の面でも大きな負担となつている。また１−ア
ミノアントラキノンの臭素化反応はニトロベンゼンなど
の有機溶媒中で容易に進行することも知られているがこ
の方法も作業環境、溶媒回収、排液処理など工業的には
問題が多い。本発明者らは硫酸溶解法に代る臭素化方法
を探索した結果本発明の方法を見出した。すなわち１−
アミノアントラキノンを臭素化するにあたり、１−アミ
ノアントラキノンの結晶を２０μ以下の微粒子状として
使用すれは水性系媒体中でも容易に臭素化は進行し高純
度の１−アミノー ２ ・ ４−ジブロムアントラキノ
ンが得られる。１−アミノアントラキノンの微粒子化は
通常の粉砕機による粉体で行なつてもよいが、界面活性
剤の存在下に、湿式でコロイドミル、サンドグラインダ
ー等により微粒化し、スラリー状として使用するのが好
ましい。In this method, in order to proceed smoothly with bromination, 1-aminoanthraquinone is dissolved in sulfuric acid and then discharged into a large amount of water for dispersion. Therefore, sulfuric acid, which is not essential for the reaction, is used, and it is particularly environmentally friendly. As regulations have become stricter, wastewater treatment has become a huge burden. It is also known that the bromination reaction of 1-aminoanthraquinone proceeds easily in an organic solvent such as nitrobenzene, but this method also has many problems from an industrial perspective, such as the working environment, solvent recovery, and wastewater treatment. The present inventors searched for a bromination method to replace the sulfuric acid dissolution method and discovered the method of the present invention. That is, 1-
When brominating aminoanthraquinone, if crystals of 1-aminoanthraquinone are used in the form of fine particles of 20μ or less, bromination can easily proceed even in an aqueous medium, yielding highly pure 1-aminoanthraquinone. It will be done. Although 1-aminoanthraquinone can be made into fine particles using an ordinary grinder, it is preferable to make it into fine particles using a wet colloid mill, sand grinder, etc. in the presence of a surfactant, and then use it as a slurry. preferable.
反応を円滑に進行させるためには２０μ以下の微粒子状
とすればよいが１〜１０μ程度が特に好”ましく、また
微粒化及び反応を円滑に進行させるのに通常のノニオン
系及びアニオン系の界面活性剤の併用が有効である。も
ちろん微粒化しながら臭素を作用させて微粒化と臭素化
を同時に行なうことも可能である。本発明の方法によれ
ば大量の硫酸又は発煙硫酸を使用することなく高純度の
１−アミノー２ ・ ４ージブロムアントラキノンを得
ることができる。In order for the reaction to proceed smoothly, fine particles of 20 μm or less are sufficient, but particles of about 1 to 10 μm are particularly preferable. It is effective to use a surfactant in combination.Of course, it is also possible to simultaneously perform atomization and bromination by applying bromine while atomizing.According to the method of the present invention, a large amount of sulfuric acid or fuming sulfuric acid can be used. It is possible to obtain highly pure 1-amino-2-4-dibromoanthraquinone.
以下本発明の方法を実施例により説明する。実施例１純
度９８％の１−アミノアントラキノン１０００ｙをナフ
タリンスルホン酸ホルマリン縮合物１０ｙおよび水１０
００ｙと混合しサンドグラインダーにより１ーアミノア
ントラキノンの結晶の９５％以上が５μ以下になるまで
微粒化した。The method of the present invention will be explained below with reference to Examples. Example 1 1000 y of 1-aminoanthraquinone with a purity of 98% was mixed with 10 y of naphthalene sulfonic acid formalin condensate and 10 y of water.
00y and atomized using a sand grinder until 95% or more of the 1-aminoanthraquinone crystals had a size of 5μ or less.
この微粒化液１９８ｙ（１−アミノアントラキノン１０
０ｙを含む）と水８００ｙを反応機に装入し、次いで３
〜４時間で徐々に臭素９３ｙ１３５％塩酸１４５ダ、２
０％塩素酸ナトリウム水溶液１００ｙを順次滴下装入し
た。This atomization liquid 198y (1-aminoanthraquinone 10
0y) and 800y of water were charged into the reactor, and then 3
bromine 93y 135% hydrochloric acid 145 da, 2
100 y of 0% sodium chlorate aqueous solution was sequentially added dropwise.
Claims (1)
−２・４−ジブロムアントラキノンを製造する際に、１
−アミノアントラキノンの結晶を機械的にあらかじめ微
粒化したのちあるいは微粒化しながら、水性系媒体中で
臭素を作用させることを特徴とする１−アミノ−２・４
−ジブロムアントラキノンの製造方法。1 When producing 1-amino-2,4-dibromoanthraquinone by brominating 1-aminoanthraquinone, 1
- 1-amino-2.4 characterized in that the crystals of aminoanthraquinone are mechanically atomized in advance or while being atomized, and then bromine is applied in an aqueous medium.
- A method for producing dibromoanthraquinone.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4841377A JPS6042785B2 (en) | 1977-04-28 | 1977-04-28 | Method for producing 1-amino-2,4-dibromanthraquinone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4841377A JPS6042785B2 (en) | 1977-04-28 | 1977-04-28 | Method for producing 1-amino-2,4-dibromanthraquinone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS53135961A JPS53135961A (en) | 1978-11-28 |
| JPS6042785B2 true JPS6042785B2 (en) | 1985-09-25 |
Family
ID=12802609
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4841377A Expired JPS6042785B2 (en) | 1977-04-28 | 1977-04-28 | Method for producing 1-amino-2,4-dibromanthraquinone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6042785B2 (en) |
-
1977
- 1977-04-28 JP JP4841377A patent/JPS6042785B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS53135961A (en) | 1978-11-28 |
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