JPH01160948A - Production of 3,5-diamino-2,4,6-triiodobenzoic acid - Google Patents
Production of 3,5-diamino-2,4,6-triiodobenzoic acidInfo
- Publication number
- JPH01160948A JPH01160948A JP31871087A JP31871087A JPH01160948A JP H01160948 A JPH01160948 A JP H01160948A JP 31871087 A JP31871087 A JP 31871087A JP 31871087 A JP31871087 A JP 31871087A JP H01160948 A JPH01160948 A JP H01160948A
- Authority
- JP
- Japan
- Prior art keywords
- hydrochloric acid
- reaction
- acid
- diamino
- iodine
- 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〕
本発明の方法により得られる３、５−ジアミノ−２，４
゜６−トリヨード安息香酸は、静脈内毒性が極めて低い
、レントゲン造影剤の中間体として用いられている。Detailed Description of the Invention [Industrial Field of Application] 3,5-diamino-2,4 obtained by the method of the present invention
6-Triiodobenzoic acid has extremely low intravenous toxicity and is used as an intermediate for X-ray contrast agents.
３．５−ジアミノ−２，４，６−トリヨード安息香酸は
、３．５−ジアミノ安息香酸を酸性溶媒中、例えば塩酸
水溶液中で一塩化沃素を適当な溶媒、例えば塩酸水溶液
、塩化ナトリウム水？８液、塩化カリウム水溶液に溶解
させて反応系内に投入することにより沃素化される（特
公昭３４−６２ 、ジャーナル・オブ・ゼ・アメリカン
・ケミカル・ソサイアティ（Ｊｏｕｒｎａｌ ｏｆ ｔ
ｈｅ Ａｍｅｒｉｃａｎ Ｃｈｅｍｉｃａｌ ５ｏｃｉ
ｅｔｙ）Ｖｏｌ、７８．３２１０−３２１６．１９５６
）。3.5-diamino-2,4,6-triiodobenzoic acid can be prepared by mixing 3.5-diaminobenzoic acid in an acidic solvent, such as an aqueous solution of hydrochloric acid, and adding iodine monochloride in an appropriate solvent, such as an aqueous solution of hydrochloric acid, an aqueous sodium chloride solution, etc. 8 liquid, dissolved in an aqueous potassium chloride solution and introduced into the reaction system to iodide (Special Publication 34-62, Journal of the American Chemical Society)
he American Chemical
ety) Vol, 78.3210-3216.1956
).
〔発明が解決しようとする問題点］
３．５−ジアミノ−２，４，６−１−リョード安患香酸
は、３．５−ジアミノ安息香酸を一塩化沃素により沃素
化させて得られるが、沃素化の際に一塩化沃素１モルに
対して１モルの塩化水素が副生する。[Problems to be solved by the invention] 3.5-diamino-2,4,6-1-lyodobenzoic acid is obtained by iodinating 3.5-diaminobenzoic acid with iodine monochloride. During iodination, 1 mol of hydrogen chloride is produced as a by-product per 1 mol of iodine monochloride.
３．５−ジアミノ安息香酸から３，５−ジアミノ−２，
４，６−トリヨード安息香酸を１モル製造するためには
、最低３モルの一塩化沃素が必要となる。そのため３モ
ルの塩化水素が副生ずることになる。３．５−ジアミノ
−２，４，６−トリヨード安息香酸を結晶として取り出
した後の、この副生じた塩化水素を含んだ反応液は、廃
液として処理する場合に、公害対策等のために極めて不
経済的な製造方法となる。3,5-diamino-2, from 3,5-diaminobenzoic acid
To produce 1 mole of 4,6-triiodobenzoic acid, a minimum of 3 moles of iodine monochloride is required. Therefore, 3 moles of hydrogen chloride will be produced as a by-product. After extracting 3.5-diamino-2,4,6-triiodobenzoic acid as crystals, the reaction solution containing by-produced hydrogen chloride should be treated as a waste solution with extreme pollution control measures. This becomes an uneconomical manufacturing method.
〔問題点を解決するための手段及び作用〕本発明者らは
、前記の問題点を解決するために鋭意検討した結果、−
塩化沃素の溶媒として塩酸水溶液を用いた場合は、その
塩酸を濃縮により回収し、繰り返し反応に使用すること
によって本発明の目的を達成できることを見出し、本発
明を完成させるに至った。[Means and effects for solving the problems] As a result of intensive studies to solve the above problems, the present inventors have found that -
The present inventors have discovered that when an aqueous hydrochloric acid solution is used as a solvent for iodine chloride, the object of the present invention can be achieved by recovering the hydrochloric acid by concentration and repeatedly using it in reactions, and has completed the present invention.
即ち、本発明は、
３．５−ジアミノ−２，４，６−トリヨード安息香酸の
製造において、反応系からの塩酸を濃縮・回収し、繰り
返し反応に用いることを特徴とする３、５−ジアミノ−
２，４，６−トリヨード安息香酸の製造方法である。That is, the present invention provides a method for producing 3,5-diamino-2,4,6-triiodobenzoic acid, which is characterized in that hydrochloric acid from the reaction system is concentrated and recovered and used for repeated reactions. −
This is a method for producing 2,4,6-triiodobenzoic acid.
以下、本発明の詳細な説明する。The present invention will be explained in detail below.
本発明の方法により、塩酸水溶液中で沃素化剤として一
塩化沃素を作用させて、３，５−ジアミノ安息香酸から
３．５−ジアミノ−２，４，６−トリヨード安息香酸を
製造するにあたり、３．５−ジアミノ−２，４，６−ト
リヨード安息香酸の結晶濾別後の濾液を活性炭で処理し
、微量の沃素及び有機物を除去し、濃縮の後、高濃度の
塩酸を回収し、次の反応のための溶媒として繰り返し用
いることで、廃液処理を簡略化でき、また原単位も改善
することができる。According to the method of the present invention, in producing 3,5-diamino-2,4,6-triiodobenzoic acid from 3,5-diaminobenzoic acid by reacting iodine monochloride as an iodizing agent in an aqueous hydrochloric acid solution, 3. The filtrate after crystal filtration of 5-diamino-2,4,6-triiodobenzoic acid is treated with activated carbon to remove trace amounts of iodine and organic matter, and after concentration, highly concentrated hydrochloric acid is recovered. By repeatedly using it as a solvent for the reaction, waste liquid treatment can be simplified and the consumption rate can also be improved.
前記塩酸からの活性炭による微量の有機物及び沃素の除
去は、濃縮前に行うことが望ましい、その理由は、微量
の沃素の昇華による、反応器の腐食を防ぐためである。It is desirable to remove trace amounts of organic matter and iodine from the hydrochloric acid using activated carbon before concentration, in order to prevent corrosion of the reactor due to sublimation of trace amounts of iodine.
この活性炭処理による沃素等の不要成分の除去は、繰り
返し利用するには特に効果的である。この活性炭の添加
量は、濾液に対して１〜５重量％でよい。Removal of unnecessary components such as iodine by this activated carbon treatment is particularly effective for repeated use. The amount of activated carbon added may be 1 to 5% by weight based on the filtrate.
本発明での前記塩酸の濃縮は、常圧濃縮で行う。Concentration of the hydrochloric acid in the present invention is carried out under normal pressure.
濃縮温度は１００〜１０９℃の範囲が望ましく、この温
度内で濃縮を行うと、留分中に殆ど塩酸が混入すること
なく濃縮することができる。The concentration temperature is desirably in the range of 100 to 109°C, and when concentration is performed within this temperature, the fraction can be concentrated with almost no hydrochloric acid mixed in.
３．５−ジアミノ安息香酸から３．５−ジアミノ−２，
４，６−トリヨード安息香酸を製造するための方法は公
知の条件に基づく。好ましい反応温度は１０〜３０゛Ｃ
である。この反応において上記した塩酸を用いる。3.5-diamino-2, from 3.5-diaminobenzoic acid
The method for producing 4,6-triiodobenzoic acid is based on known conditions. The preferred reaction temperature is 10~30°C
It is. In this reaction, the above-mentioned hydrochloric acid is used.
以下、本発明を実施例により具体的に説明する。 Hereinafter, the present invention will be specifically explained with reference to Examples.
３．５−ジアミノ〜２，４．６− トリヨード安息香酸
の純度の分析法は、中和滴定による。The purity analysis method for 3,5-diamino to 2,4,6-triiodobenzoic acid is based on neutralization titration.
実施例１
３．５−ジアミノ安息香酸３０．４ｇ（０，２モル）を
水６００ｇと濃塩酸４１．２ｇからなる溶液に溶かした
。この溶液に、−塩化沃素９７．４ｇ（０，６モル）を
６Ｎ塩酸１４０ｇに溶解させて得られた溶液を１時間か
けて滴下し、更に室温で３時間攪拌した。析出した結晶
を濾別し、水でリンスした。Example 1 30.4 g (0.2 mol) of 3,5-diaminobenzoic acid was dissolved in a solution consisting of 600 g of water and 41.2 g of concentrated hydrochloric acid. A solution obtained by dissolving 97.4 g (0.6 mol) of iodine chloride in 140 g of 6N hydrochloric acid was added dropwise to this solution over 1 hour, and the mixture was further stirred at room temperature for 3 hours. The precipitated crystals were filtered off and rinsed with water.
結晶は減圧乾燥で６時間乾燥した。この時得られた濾液
８１６．３ｇを活性炭１６．３ｇで処理し、沃素及び有
機物を除去した。次に、この濾液を１００〜１０３°Ｃ
で濃縮し、１９．５％の塩酸水溶液２９１．５ｇを得た
。The crystals were dried under reduced pressure for 6 hours. 816.3 g of the filtrate obtained at this time was treated with 16.3 g of activated carbon to remove iodine and organic matter. Next, this filtrate was heated to 100-103°C.
The mixture was concentrated to obtain 291.5 g of a 19.5% aqueous hydrochloric acid solution.
この濃縮液を用いて一連の操作を５回繰り返した。結果
を表１に示す。The series of operations was repeated five times using this concentrated solution. The results are shown in Table 1.
表１
なお、この繰り返しの操作では、新規に塩酸を加えるこ
とはなかった。Table 1 Note that in this repeated operation, no new hydrochloric acid was added.
３．５−ジアミノ−２，４，６−トリヨード安息香酸を
製造する際に、結晶を濾別した後の濾液から、塩酸を回
収し、繰り返し反応に使用することにより、３．５−ジ
アミノ−２，４，６−トリヨード安息香酸を効率良く製
造できる。When producing 3.5-diamino-2,4,6-triiodobenzoic acid, hydrochloric acid is recovered from the filtrate after filtering off the crystals and used in repeated reactions to produce 3.5-diamino- 2,4,6-triiodobenzoic acid can be efficiently produced.
特許出願人 三井東圧化学株式会社Patent applicant Mitsui Toatsu Chemical Co., Ltd.
Claims (1)
酸の製造において、反応系からの塩酸を濃縮・回収し、
繰り返し反応に用いることを特徴とする３，５−ジアミ
ノ−２，４，６−トリヨード安息香酸の製造方法。1) In the production of 3,5-diamino-2,4,6-triiodobenzoic acid, concentrate and collect hydrochloric acid from the reaction system,
A method for producing 3,5-diamino-2,4,6-triiodobenzoic acid, which is characterized in that it is used in repeated reactions.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31871087A JPH01160948A (en) | 1987-12-18 | 1987-12-18 | Production of 3,5-diamino-2,4,6-triiodobenzoic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31871087A JPH01160948A (en) | 1987-12-18 | 1987-12-18 | Production of 3,5-diamino-2,4,6-triiodobenzoic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01160948A true JPH01160948A (en) | 1989-06-23 |
Family
ID=18102121
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP31871087A Pending JPH01160948A (en) | 1987-12-18 | 1987-12-18 | Production of 3,5-diamino-2,4,6-triiodobenzoic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01160948A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114213268A (en) * | 2021-12-27 | 2022-03-22 | 安康市农业科学研究院 | Method for synthesizing diatrizoic acid key intermediate |
-
1987
- 1987-12-18 JP JP31871087A patent/JPH01160948A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114213268A (en) * | 2021-12-27 | 2022-03-22 | 安康市农业科学研究院 | Method for synthesizing diatrizoic acid key intermediate |
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