JP2993856B2 - Method for producing carbazic acid - Google Patents
Method for producing carbazic acidInfo
- Publication number
- JP2993856B2 JP2993856B2 JP6300251A JP30025194A JP2993856B2 JP 2993856 B2 JP2993856 B2 JP 2993856B2 JP 6300251 A JP6300251 A JP 6300251A JP 30025194 A JP30025194 A JP 30025194A JP 2993856 B2 JP2993856 B2 JP 2993856B2
- Authority
- JP
- Japan
- Prior art keywords
- carbazic acid
- reaction
- producing
- carbon dioxide
- hydrazine
- 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 - Fee Related
Links
Description
【０００１】[0001]
【産業上の利用分野】本発明は、カルバジン酸の製造法
に関する。詳しくは、原料のヒドラジンと等モル量程度
のみの炭酸ガスを用い、ほぼ１００％に近い収量でカル
バジン酸を製造する方法に関する。カルバジン酸は公知
の化合物であり、例えば、医薬、農薬等の中間体である
メチルカルバゼートの原料として有用である。The present invention relates to a method for producing carbazic acid. More specifically, the present invention relates to a method for producing carbazic acid at a yield close to 100% using only about equimolar amount of carbon dioxide gas as hydrazine as a raw material. Carbazic acid is a known compound and is useful, for example, as a raw material for methylcarbazate, which is an intermediate for pharmaceuticals, agricultural chemicals, and the like.
【０００２】[0002]
【従来の技術】従来カルバジン酸は、常圧下にヒドラジ
ン水溶液に過剰の炭酸ガスを通じることにより製造され
ている。しかしながら、この方法では収率が６０〜７０
％程度であり、充分満足のゆく水準には達していない。
加えて炭酸ガスの使用量が多いという欠点がある。2. Description of the Related Art Conventionally, carbazic acid has been produced by passing excess carbon dioxide gas through a hydrazine aqueous solution under normal pressure. However, in this method, the yield is 60-70.
%, Which has not yet reached a satisfactory level.
In addition, there is a disadvantage that a large amount of carbon dioxide is used.
【０００３】[0003]
【発明が解決しようとする課題】本発明の目的は、収率
がほぼ１００％に達し、炭酸ガスの使用量も少なくてす
む新規なカルバジン酸の製造法を提供することにある。SUMMARY OF THE INVENTION An object of the present invention is to provide a novel method for producing carbazic acid, which can achieve a yield of almost 100% and requires a small amount of carbon dioxide gas.
【０００４】[0004]
【課題を解決するための手段】本発明はヒドラジン化合
物又はその水溶液と液状炭酸ガスを加圧下に反応させる
ことを特徴とするカルバジン酸の製造法に係る。The present invention relates to a method for producing carbazic acid, which comprises reacting a hydrazine compound or an aqueous solution thereof with liquid carbon dioxide under pressure.
【０００５】本発明において、ヒドラジン化合物として
は公知のものが使用できるが、例えば、ヒドラジン、ヒ
ドラジンヒドラート等が好ましい。本発明の反応は、加
圧下に行われる。この時、圧力は特に制限されないが、
通常１０〜６０kg／cm2程度、好ましくは１０〜４５kg
／cm2程度とすればよい。本反応は、通常−３０〜３０
℃程度、好ましくは−３０〜１０℃程度の温度下に行わ
れ、通常１〜２時間程度で終了する。また本反応は、好
ましくは撹拌下に行われる。In the present invention, known compounds can be used as the hydrazine compound. For example, hydrazine, hydrazine hydrate and the like are preferable. The reaction of the present invention is performed under pressure. At this time, the pressure is not particularly limited,
Usually about 10-60 kg / cm 2 , preferably 10-45 kg
/ Cm 2 . This reaction is usually carried out at -30 to 30.
C., preferably at a temperature of about -30.degree. C. to about 10.degree. This reaction is preferably performed with stirring.
【０００６】本反応に於けるヒドラジン化合物と液状炭
酸ガスの使用割合は特に制限されず、広い範囲から適宜
選択できるが、経済性等を考慮すると等モル量程度で充
分である。なお、本反応においては、反応系内にドライ
アイスを入れ、適当な温度条件で液化させた後、反応を
行ってもよい。本反応により得られるカルバジン酸は、
濾過、有機溶媒による洗浄等の通常の手段に従って、反
応系から容易に単離精製することができる。The ratio of the hydrazine compound and the liquid carbon dioxide used in the reaction is not particularly limited and can be appropriately selected from a wide range. However, in consideration of economy and the like, an equimolar amount is sufficient. In this reaction, the reaction may be carried out after putting dry ice into the reaction system and liquefying it under appropriate temperature conditions. The carbazic acid obtained by this reaction is
It can be easily isolated and purified from the reaction system according to ordinary means such as filtration and washing with an organic solvent.
【０００７】[0007]
【実施例】以下に実施例を挙げ、本発明を具体的に説明
する。 実施例１ 撹拌機、温度計及び圧力計を備えた５００ml容のステン
レス製密封圧力容器に、１００％ヒドラジンヒドラート
１００g（２モル）を０〜５℃に冷却しながら仕込ん
だ。次いで、撹拌下に液化炭酸ガス ９２.４g（２モ
ル）を仕込んだ。この時、容器内の圧力は３５kg／cm2
となった。１時間撹拌した後、反応を停止した。反応液
を濾過して固形物を濾取し、メタノールで洗浄し、乾燥
し、カルバジン酸の白色結晶 ７４.５gを得た。ヒドラ
ジンヒドラートよりの収率は９８％であった。この結晶
について、融点、ＩＲスペクトル、ＮＭＲスペクトル、
及びマススペクトルを測定したところ、従来法で別途合
成したカルバジン酸の標品と完全に一致した。EXAMPLES The present invention will be specifically described below with reference to examples. Example 1 100 g (2 mol) of 100% hydrazine hydrate was charged into a sealed 500-ml stainless steel pressure vessel equipped with a stirrer, a thermometer and a pressure gauge while cooling to 0 to 5 ° C. Next, 92.4 g (2 mol) of liquefied carbon dioxide gas was charged under stirring. At this time, the pressure in the container was 35 kg / cm 2
It became. After stirring for 1 hour, the reaction was stopped. The reaction mixture was filtered and the solid was collected by filtration, washed with methanol and dried to obtain 74.5 g of white crystals of carbazic acid. The yield from hydrazine hydrate was 98%. About this crystal, melting point, IR spectrum, NMR spectrum,
When the mass spectrum was measured, it completely coincided with the carbazic acid sample separately synthesized by the conventional method.
【０００８】実施例２〜４ 表１に示す様に反応温度と反応時間を変える以外は、実
施例１と同様に操作し、カルバジン酸を製造した。表１
に収率を併記する。Examples 2 to 4 Carbazic acid was produced in the same manner as in Example 1 except that the reaction temperature and the reaction time were changed as shown in Table 1. Table 1
The yield is also shown in Table 2.
【０００９】[0009]
【表１】 [Table 1]
【００１０】実施例５ 撹拌機、温度計及び圧力計を備えた５００ml容のステン
レス製密封圧力容器に、ドライアイス ９２.４g（２.１
モル）を仕込んだ。次いで、１００％ヒドラジンヒドラ
ート １００g（２モル）を０〜５℃に冷却しながら仕込
んだ。その温度を維持しながら、引き続き２時間撹拌し
て反応を行った後、反応を停止した。得られた反応液か
ら固形物を濾取し、メタノールで洗浄し、乾燥し、カル
バジン酸の白色結晶 ７４.５gを得た。ヒドラジンヒド
ラートよりの収率は９８％であった。EXAMPLE 5 92.4 g (2.1) of dry ice was placed in a 500 ml sealed stainless steel pressure vessel equipped with a stirrer, a thermometer and a pressure gauge.
Mol). Subsequently, 100 g (2 mol) of 100% hydrazine hydrate was charged while cooling to 0 to 5 ° C. While maintaining the temperature, the reaction was continued by stirring for 2 hours, and then the reaction was stopped. A solid substance was collected by filtration from the obtained reaction solution, washed with methanol, and dried to obtain 74.5 g of white crystals of carbazic acid. The yield from hydrazine hydrate was 98%.
【００１１】[0011]
【発明の効果】本発明の方法によれば、ほぼ１００％の
収率で目的とするカルバジン酸を製造することができ、
炭酸ガスの消費量も従来の方法より著しく少なくて済
む。According to the method of the present invention, the target carbazic acid can be produced with a yield of almost 100%.
The consumption of carbon dioxide is also significantly lower than in conventional methods.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 名村 聡 徳島県徳島市川内町加賀須野463 大塚 化学株式会社徳島工場内 (56)参考文献 Ｃｈｅｍｉｃａｌ Ａｂｓｔｒａｃｔ ｓ，Ｎｏ．103：226253（1985) (58)調査した分野(Int.Cl.6，ＤＢ名) C07C 281/02 ＣＡ（ＳＴＮ)────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Satoshi Namura 463 Kagasuno, Kawauchi-machi, Tokushima City, Tokushima Prefecture Inside the Otsuka Chemical Co., Ltd. Tokushima Plant (56) References Chemical Abstracts, No. 103: 226253 (1985) (58) Fields investigated (Int. Cl. 6 , DB name) C07C 281/02 CA (STN)
Claims (2)
炭酸ガスを加圧下に反応させることを特徴とするカルバ
ジン酸の製造法。1. A method for producing carbazic acid, comprising reacting a hydrazine compound or an aqueous solution thereof with liquid carbon dioxide under pressure.
炭酸ガスを導入する請求項１の製造法。2. The method according to claim 1, wherein liquid carbon dioxide gas is introduced in an equimolar amount with the hydrazine compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6300251A JP2993856B2 (en) | 1994-11-08 | 1994-11-08 | Method for producing carbazic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6300251A JP2993856B2 (en) | 1994-11-08 | 1994-11-08 | Method for producing carbazic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH08134038A JPH08134038A (en) | 1996-05-28 |
| JP2993856B2 true JP2993856B2 (en) | 1999-12-27 |
Family
ID=17882537
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6300251A Expired - Fee Related JP2993856B2 (en) | 1994-11-08 | 1994-11-08 | Method for producing carbazic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2993856B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101282751B1 (en) * | 2010-12-27 | 2013-07-05 | 서강대학교산학협력단 | Method for Producing Solid Carbazic Acid Derivative Powder |
| KR101363595B1 (en) * | 2012-03-12 | 2014-02-17 | 서강대학교산학협력단 | Products from Reactions of Hydrazine Derivatives with Carbon Dioxide |
| CN103980164B (en) * | 2014-04-26 | 2015-08-19 | 华北电力大学（保定） | A kind of method of synthesizing carbazic acid alcohol ester |
-
1994
- 1994-11-08 JP JP6300251A patent/JP2993856B2/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| Ｃｈｅｍｉｃａｌ Ａｂｓｔｒａｃｔｓ，Ｎｏ．１０３：２２６２５３（１９８５） |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH08134038A (en) | 1996-05-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |